Abstract
During the last decade, there has been an impressive amount of new reactions catalyzed by gold (I or III) complexes, many of which lead to oxygen heterocycles in novel, practical, and efficient ways. In this chapter we have selected the most representative examples of the use of gold catalysis for the synthesis of oxygenated heterocycles, with an organization based on the type of reaction. Each section pretends to give an overview of the potential of each particular strategy and its usefulness to prepare synthetically relevant oxygenated rings. Heterocyclic systems that contain other heteroatoms in addition to oxygen have been essentially excluded, as well as those examples in which the oxygen atoms merely acts as a connecting element between two reactive functional groups.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Notes
References
Elliott MC (2000) Saturated oxygen heterocycles. J Chem Soc Perkin Trans 1:1291–1318
Elliot MC, Williams E (2001) J Chem Soc Perkin Trans 1 2303
Alali FQ, Liu XX, McLaughlin JL (1999) J Nat Prod 62:504
Boivin TLB (1987) Tetrahedron 43:3309
Wuitschik G, Carreira EM, Wagner B, Fischer H, Parrilla I, Schuler F, Rogers-Evans M, Müller K (2010) Oxetanes in drug discovery: structural and synthetic insights. J Med Chem 53:3227–3246
Maes BUW, Cossy J (eds) (2014) Synthesis of saturated oxygenated heterocycles I, vol 36, Topics in heterocyclic chemistry. Springer, Berlin
Cardillo G, Orena M (1990) Stereocontrolled cyclofunctionalizations of double bonds through heterocyclic intermediates. Tetrahedron 46:3321–3408
Maes BUW, Cossy J (eds) (2014) Synthesis of saturated oxygenated heterocycles II, vol 36, Topics in heterocyclic chemistry. Springer, New York
Toste FD, Michelet V (eds) (2015) Gold catalysis: an homogeneous approach (catalytic science series). Imperial College Press, London
Hashmi ASK, Toste FD (eds) (2012) Modern gold catalyzed synthesis. Wiley, Weinheim
Mohr F (ed) (2009) Gold chemistry. Wiley, Weinheim
Slaughter LM (ed) (2015) Homogeneous gold catalysis, Topics in current chemistry, vol 357. Springer, Cham
Gorin DJ, Toste FD (2007) Relativistic effects in homogeneous gold catalysis. Nature 446:395–403
Fürstner A, Davies PW (2007) Catalytic carbophilic activation: catalysis by platinum and gold pi acids. Angew Chem Int Ed 46:3410–3449
Huguet N, Echavarren AM (2013) Gold-catalyzed O-H bond addition to unsaturated organic molecules. In: Ananikov VP, Tanaka M (eds) Hydrofunctionalization, vol 43, Topics in organometallic chemistry., pp 291–324
Hashmi ASK, Buehrle M (2010) Gold-catalyzed addition of X-H bonds to C-C multiple bonds. Aldrichimica Acta 43:27–33
Corma A, Leyva-Pérez A, Sabater MJ (2011) Gold-catalyzed carbon-heteroatom bond-forming reactions. Chem Rev 111:1657–1712
Patil NT, Kavthe RD, Shinde VS (2012) Transition metal-catalyzed addition of C-, N- and O-nucleophiles to unactivated C-C multiple bonds. Tetrahedron 68:8079–8146
Krause N, Winter C (2011) Gold-catalyzed nucleophilic cyclization of functionalized allenes: a powerful access to carbo- and heterocycles. Chem Rev 111:1994–2009
Yang W, Hashmi ASK (2014) Mechanistic insights into the gold chemistry of allenes. Chem Soc Rev 43:2941–2955
Hoffmann-Roder A, Krause N (2001) Gold(III) chloride catalyzed cyclization of alpha-hydroxyallenes to 2,5-dihydrofurans. Org Lett 3:2537–2538
Winter C, Krause N (2009) Towards sustainable homogeneous gold catalysis: cycloisomerization of functionalized allenes in water. Green Chem 11:1309–1312
Gockel B, Krause N (2006) Golden times for allenes: gold-catalyzed cycloisomerization of beta-hydroxyallenes to dihydropyrans. Org Lett 8:4485–4488
Gockel B, Krause N (2010) Synthesis of bicyclic ethers by a gold/palladium/gold-catalyzed cyclization/cross coupling sequence. Eur J Org Chem 2010:311–316
Zriba R, Gandon V, Aubert C, Fensterbank L, Malacria M (2008) Alkyne versus allene activation in platinum- and gold-catalyzed cycloisomerization of hydroxylated 1,5-allenynes. Chem Eur J 14:1482–1491
Eom D, Kang D, Lee PH (2010) Synthesis of 2-alkyl- and ary1-3-ethoxycarbony1-2,5-dihydrofurans through gold-catalyzed intramolecular hydroalkoxylation. J Org Chem 75:7447–7450
Kim S, Lee PH (2008) Cyclization of allenyne-1,6-diols catalyzed by gold and silver salts: an efficient selective synthesis of dihydrofuran and furan derivatives. Adv Synth Catal 350:547–551
Aksιn Ö, Krause N (2008) Gold-catalyzed synthesis of 2,5-dihydrofurans in ionic liquids. Adv Synth Catal 350:1106–1112
Alcaide B, Almendros P, Martinez del Campo T, Fernandez I (2011) Fascinating reactivity in gold catalysis: synthesis of oxetenes through rare 4-exo-dig allene cyclization and infrequent beta-hydride elimination. Chem Commun 47:9054–9056
Zhang ZB, Liu C, Kinder RE, Han XQ, Qian H, Widenhoefer RA (2006) Highly active Au(I) catalyst for the intramolecular exo-hydrofunctionalization of allenes with carbon, nitrogen, and oxygen nucleophiles. J Am Chem Soc 128:9066–9073
Alcaide B, Almendros P, del Campo TM, Soriano E, Marco-Contelles JL (2009) Regioselectivity control in the metal-catalyzed o-c functionalization of gamma-allenols, part 1: experimental study. Chem Eur J 15:1901–1908
Alcaide B, Almendros P (2011) Gold-catalyzed heterocyclizations in alkynyl- and allenyl-beta-lactams. Beilstein J Org Chem 7:622–630
Alcaide B, Almendros P (2014) Gold-catalyzed cyclization reactions of allenol and alkynol derivatives. Acc Chem Res 47:939–952
Alcaide B, Almendros P, del Campo TM, Soriano E, Marco-Contelles JL (2009) Metal-catalyzed cyclization of β- and γ-allenols derived from d-glyceraldehyde-synthesis of enantiopure dihydropyrans and tetrahydrooxepines: an experimental and theoretical study. Chem Eur J 15:9127–9138
Zhang Z, Widenhoefer RA (2007) Gold(I)-catalyzed intramolecular enantioselective hydroalkoxylation of allenes. Angew Chem Int Ed 46:283–285
Hamilton GL, Kang EJ, Mba M, Toste FD (2007) A powerful chiral counterion strategy for asymmetric transition metal catalysis. Science 317:496–499
Zi W, Toste FD (2015) Gold(I)-catalyzed enantioselective desymmetrization of 1,3-diols through intramolecular hydroalkoxylation of allenes. Angew Chem Int Ed. 10.1002/anie.201508331
Cox N, Uehling MR, Haelsig KT, Lalic G (2013) Catalytic asymmetric synthesis of cyclic ethers containing an alpha-tetrasubstituted stereocenter. Angew Chem Int Ed 52:4878–4882
Volz F, Krause N (2007) Golden opportunities in natural product synthesis: first total synthesis of (-)-isocyclocapitelline and (-)-isochrysotricine by gold-catalyzed allene cycloisomerization. Org Biomol Chem 5:1519–1521
Volz F, Wadman SH, Hoffmann-Roder A, Krause N (2009) Gold catalysis in stereoselective natural product synthesis: (+)-linalool oxide, (-)- isocyclocapitelline, and (-)-isochrysotricine. Tetrahedron 65:1902–1910
Gao ZH, Li YF, Cooksey JP, Snaddon TN, Schunk S, Viseux EME, McAteer SM, Kocienski PJ (2009) A synthesis of an ionomycin calcium complex. Angew Chem Int Ed 48:5022–5025
Sawama Y, Sawama Y, Krause N (2008) First total synthesis of (R, R, R)- and (3R,5S,9R)-bejarol by gold-catalyzed allene cycloisomerization and determination of absolute configuration of the natural product. Org Biomol Chem 6:3573–3579
Kang J-E, Lee E-S, Park S-I, Shin S (2005) Gold-catalyzed cyclization of tert-butyl allenoate: general synthesis of 2,4-functionalized butenolides. Tetrahedron Lett 46:7431–7433
Liu L-P, Xu B, Mashuta MS, Hammond GB (2008) Synthesis and structural characterization of stable organogold(I) compounds. Evidence for the mechanism of gold-catalyzed cyclizations. J Am Chem Soc 130:17642–17643
Piera J, Krumlinde P, Strübing D, Bäckvall J-E (2007) Gold-catalyzed cyclization of allene-substituted malonate esters: synthesis of β, γ-unsaturated δ-lactones. Org Lett 9:2235–2237
Alcaide B, Almendros P, Miguel Alonso J (2011) Gold catalyzed oxycyclizations of alkynols and alkyndiols. Org Biomol Chem 9:4405–4416
Goodwin JA, Aponick A (2015) Regioselectivity in the Au-catalyzed hydration and hydroalkoxylation of alkynes. Chem Commun 51:8730–8741
Dorel R, Echavarren AM (2015) Gold(I)-catalyzed activation of alkynes for the construction of molecular complexity. Chem Rev 115:9028–9072
Harkat H, Weibel JM, Pale P (2007) Synthesis of functionalized THF and THP through Au-catalyzed cyclization of acetylenic alcohols. Tetrahedron Lett 48:1439–1442
Harkat H, Blanc A, Weibel J-M, Pale P (2008) Versatile and expeditious synthesis of aurones via aul-catalyzed cyclization. J Org Chem 73:1620–1623
Zhdanko A, Maier ME (2015) Explanation of “silver effects” in gold(I)-catalyzed hydroalkoxylation of alkynes. ACS Catal 5:5994–6004
Zhdanko A, Maier ME (2014) Explanation of counterion effects in gold(I)-catalyzed hydroalkoxylation of alkynes. ACS Catal 4:2770–2775
Trost BM, Dong GB (2008) Total synthesis of bryostatin 16 using atom-economical and chemoselective approaches. Nature 456:485–488
Rüttinger R, Leutzow J, Wilsdorf M, Wilckens K, Czekelius C (2011) Reversal of selectivity in gold-catalyzed cyclizations of 3,3-disubstituted 1,4-diynes. Org Lett 13:224–227
Wilckens K, Uhlemann M, Czekelius C (2009) Gold-catalyzed endo-cyclizations of 1,4-diynes to seven-membered ring heterocycles. Chem Eur J 15:13323–13326
Murai M, Uenishi J, Uemura M (2010) Gold(I)-catalyzed asymmetric synthesis of planar chiral arene chromium complexes. Org Lett 12:4788–4791
Hashmi ASK, Häffner T, Rudolph M, Rominger F (2011) Cyclization of 2-alkynylallyl alcohols to highly substituted furans by gold(I)–carbene complexes. Eur J Org Chem 2011:667–671
Kim S, Kang D, Shin S, Lee PH (2010) Gold-catalyzed cyclization of enyne-1,6-diols to substituted furans. Tetrahedron Lett 51:1899–1901
Genin E, Toullec PY, Antoniotti S, Brancour C, Genet JP, Michelet W (2006) Room temperature Au(I)-catalyzed exo-selective cycloisomerization of acetylenic acids: an entry to functionalized gamma-lactones. J Am Chem Soc 128:3112–3113
Harkat H, Weibel JM, Pale P (2006) A mild access to gamma- or delta-alkylidene lactones through gold catalysis. Tetrahedron Lett 47:6273–6276
Harkat H, Dembele AY, Weibel JM, Blanc A, Pale P (2009) Cyclization of alkynoic acids with gold catalysts: a surprising dichotomy between Au-I and Au-III. Tetrahedron 65:1871–1879
Michelet V, Toullec PY, Genin E, Antoniotti S, Genet JP (2008) Au2O3 as a stable and efficient catalyst for the selective cycloisomerization of gamma-acetylenic carboxylic acids to gamma-alkylidene-gamma-butyrolactones. Synlett 707–711
Tomas-Mendivil E, Toullec PY, Borge J, Conejero S, Michelet V, Cadierno V (2013) Water-soluble gold(I) and gold(III) complexes with sulfonated N-heterocyclic carbene ligands: synthesis, characterization, and application in the catalytic cycloisomerization of gamma-alkynoic acids into enol-lactones. ACS Catal 3:3086–3098
Marchal E, Uriac P, Legouin B, Toupet L, van de Weghe P (2007) Cycloisomerization of γ- and δ-acetylenic acids catalyzed by gold(I) chloride. Tetrahedron 63:9979–9990
Chaladaj W, Corbet M, Fürstner A (2012) Total synthesis of neurymenolide a based on a gold-catalyzed synthesis of 4-hydroxy-2-pyrones. Angew Chem Int Ed 51:6929–6933
Kang J-E, Shin S (2006) Au(I)-catalyzed cyclization of tert-butyl carbonates derived from homopropargyl alcohols: a catalytic alternative to cyclic enol carbonates. Synlett 2006:0717–0720
Chiarucci M, Bandini M (2013) New developments in gold-catalyzed manipulation of inactivated alkenes. Beilstein J Org Chem 9:2586–2614
Yang C-G, He C (2005) Gold(I)-catalyzed intermolecular addition of phenols and carboxylic acids to olefins. J Am Chem Soc 127:6966–6967
Kamiya I, Tsunoyama H, Tsukuda T, Sakurai H (2007) Lewis acid character of zero-valent gold nanoclusters under aerobic conditions: intramolecular hydroalkoxylation of alkenes. Chem Lett 36:646–647
Chandrasekhar B, Ryu J-S (2012) Gold-catalyzed intramolecular hydroalkoxylation/cyclization of conjugated dienyl alcohols. Tetrahedron 68:4805–4812
Zhang G, Cui L, Wang Y, Zhang L (2010) Homogeneous gold-catalyzed oxidative carboheterofunctionalization of alkenes. J Am Chem Soc 132:1474–1475
Sahoo B, Hopkinson MN, Glorius F (2013) Combining gold and photoredox catalysis: visible light-mediated oxy- and aminoarylation of alkenes. J Am Chem Soc 135:5505–5508
Aponick A, Li C-Y, Biannic B (2008) Au-catalyzed cyclization of monoallylic diols. Org Lett 10:669–671
Ghebreghiorgis T, Biannic B, Kirk BH, Ess DH, Aponick A (2012) The importance of hydrogen bonding to stereoselectivity and catalyst turnover in gold-catalyzed cyclization of monoallylic diols. J Am Chem Soc 134:16307–16318
Aponick A, Biannic B (2011) Chirality transfer in Au-catalyzed cyclization reactions of monoallylic diols: selective access to specific enantiomers based on olefin geometry. Org Lett 13:1330–1333
Biannic B, Aponick A (2011) Gold-catalyzed dehydrative transformations of unsaturated alcohols. Eur J Org Chem 2011:6605–6617
Aponick A, Biannic B, Jong MR (2010) A highly adaptable catalyst/substrate system for the synthesis of substituted chromenes. Chem Commun 46:6849–6851
Unsworth WP, Stevens K, Lamont SG, Robertson J (2011) Stereospecificity in the Au-catalysed cyclisation of monoallylic diols. Synthesis of (+)-isoaltholactone. Chem Commun 47:7659–7661
Hashmi ASK, Schwarz L, Choi JH, Frost TM (2000) A new gold-catalyzed C-C bond formation. Angew Chem Int Ed 39:2285–2288
Zhou CY, Chan PWH, Che CM (2006) Gold(III) porphyrin-catalyzed cycloisomerization of allenones. Org Lett 8:325–328
Sromek AW, Rubina M, Gevorgyan V (2005) 1,2-Halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans. J Am Chem Soc 127:10500–10501
Xia YZ, Dudnik AS, Gevorgyan V, Li YH (2008) Mechanistic insights into the gold-catalyzed cycloisomerization of bromoallenyl ketones: ligand-controlled regioselectivity. J Am Chem Soc 130:6940–6941
Dudnik AS, Sromek AW, Rubina M, Kim JT, Kel’in AV, Gevorgyan V (2008) Metal-catalyzed 1,2-shift of diverse migrating groups in allenyl systems as a new paradigm toward densely functionalized heterocycles. J Am Chem Soc 130:1440–1452
Li Y, Brand JP, Waser J (2013) Gold-catalyzed regioselective synthesis of 2- and 3-alkynyl furans. Angew Chem Int Ed 52:6743–6747
Belting V, Krause N (2009) Gold-catalyzed cycloisomerization of alk-4-yn-1-ones. Org Biomol Chem 7:1221–1225
Arcadi A, Alfonsi M, Chiarini M, Marinelli F (2009) Sequential gold-catalyzed reactions of 1-phenylprop-2-yn-1-ol with 1,3-dicarbonyl compounds. J Organomet Chem 694:576–582
Hashmi ASK, Sinha P (2004) Gold catalysis: mild conditions for the transformation of alkynyl epoxides to furans. Adv Synth Catal 346:432–438
Blanc A, Tenbrink K, Weibel JM, Pale P (2009) Mechanistic studies and improvement of coinage metal-catalyzed transformation of alkynyloxiranes to furans: an alcohol addition-cyclization-elimination cascade. J Org Chem 74:5342–5348
Jacques B, Hueber D, Hameury S, Braunstein P, Pale P, Blanc A, de Frémont P (2014) Synthesis, characterization, and catalytic activity of alcohol-functionalized nhc gold(i/iii) complexes. Organometallics 33:2326–2335
Ji KG, Shu XZ, Chen J, Zhao SC, Zheng ZJ, Liu XY, Liang YM (2009) Gold-catalyzed tandem cyclization/friedel-crafts type reactions toward furan derivatives. Org Biomol Chem 7:2501–2505
Michelet V (2015) Gold-catalyzed domino reactions. In: Slaughter LM (ed) Homogeneous gold catalysis, vol 357, Topics in current chemistry., pp 95–132
Inamdar SM, Konala A, Patil NT (2014) When gold meets chiral brønsted acid catalysts: extending the boundaries of enantioselective gold catalysis. Chem Commun 50:15124–15135
Kirsch SF (2008) Construction of heterocycles by the strategic use of alkyne pi-activation in catalyzed cascade reactions. Synthesis 3183–3204
Zhang LM, Kozmin SA (2005) Gold-catalyzed assembly of heterobicyclic systems. J Am Chem Soc 127:6962–6963
Toullec PY, Blarre T, Michelet V (2009) Mimicking polyolefin carbocyclization reactions: gold-catalyzed intramolecular phenoxycyclization of 1,5-enynes. Org Lett 11:2888–2891
Sethofer SG, Mayer T, Toste FD (2010) Gold(I)-catalyzed enantioselective polycyclization reactions. J Am Chem Soc 132:8276–8277
Fürstner A, Morency L (2008) On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions. Angew Chem Int Ed 47:5030–5033
Sherry BD, Maus L, Laforteza BN, Toste FD (2006) Gold(I)-catalyzed synthesis of dihydropyrans. J Am Chem Soc 128:8132–8133
Noey EL, Wang X, Houk KN (2011) Selective gold(I)-catalyzed formation of tetracyclic indolines: a single transition structure and bifurcations lead to multiple products. J Org Chem 76:3477–3483
Cera G, Crispino P, Monari M, Bandini M (2011) Stereoselective synthesis of tetracyclic indolines via gold-catalyzed cascade cyclization reactions. Chem Commun 47:7803–7805
Liu Y, Xu W, Wang X (2010) Gold(I)-catalyzed tandem cyclization approach to tetracyclic indolines. Org Lett 12:1448–1451
Barluenga J, Fernández A, Satrustegui A, Dieguez A, Rodríguez F, Fañanás FJ (2008) Tandem intramolecular hydroalkoxylation-hydroarylation reactions: synthesis of enantiopure benzofused cyclic ethers from the chiral pool. Chem Eur J 14:4153–4156
Barluenga J, Fernández A, Dieguez A, Rodríguez F, Fañanás FJ (2009) Gold- or platinum-catalyzed cascade processes of alkynol derivatives involving hydroalkoxylation reactions followed by Prins-type cyclizations. Chem Eur J 15:11660–11667
Antoniotti S, Genin E, Michelet V, Genet JP (2005) Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols. J Am Chem Soc 127:9976–9977
Santos LL, Ruiz VR, Sabater MJ, Corma A (2008) Regioselective transformation of alkynes into cyclic acetals and thioacetals with a gold(I) catalyst: comparison with brønsted acid catalysts. Tetrahedron 64:7902–7909
Liu L-P, Hammond GB (2009) Highly efficient and tunable synthesis of dioxabicyclo[4.2.1] ketals and tetrahydropyrans via gold-catalyzed cycloisomerization of 2-alkynyl-1,5-diols. Org Lett 11:5090–5092
Aponick A, Li CY, Palmes JA (2009) Au-catalyzed cyclization of monopropargylic triols: an expedient synthesis of monounsaturated spiroketals. Org Lett 11:121–124
Paioti PHS, Ketcham JM, Aponick A (2014) Controlling regiochemistry in the gold-catalyzed synthesis of unsaturated spiroketals. Org Lett 16:5320–5323
Minkler SR, Isley NA, Lippincott DJ, Krause N, Lipshutz BH (2014) Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature. Org Lett 16:724–726
Liu B, De Brabander JK (2006) Metal-catalyzed regioselective oxy-functionalization of internal alkynes: an entry into ketones, acetals, and spiroketals. Org Lett 8:4907–4910
Zhdanko A, Maier ME (2014) Gold(I)-, palladium(II)-, platinum(II)-, and Mercury(II)-catalysed spirocyclization of 1,3-enynediols: reaction scope. Eur J Org Chem 2014:3411–3422
Jaimes MCB, Bohling CRN, Serrano-Becerra JM, Hashmi ASK (2013) Highly active mononuclear NAC-gold(I) catalysts. Angew Chem Int Ed 52:7963–7966
Jaimes MCB, Rominger F, Pereira MM, Carrilho RMB, Carabineiro SAC, Hashmi ASK (2014) Highly active phosphite gold(I) catalysts for intramolecular hydroalkoxylation, enyne cyclization and furanyne cyclization. Chem Commun 50:4937–4940
Quach R, Furkert DP, Brimble MA (2013) Synthesis of benzannulated spiroacetals using chiral gold-phosphine complexes and chiral anions. Tetrahedron Lett 54:5865–5868
Yeung YY, Corey EJ (2008) A simple, efficient, and enantiocontrolled synthesis of a near-structural mimic of platensimycin. Org Lett 10:3877–3878
Fang C, Pang YC, Forsyth CJ (2010) Formal total synthesis of okadaic acid via regiocontrolled gold(I)-catalyzed spiroketalizations. Org Lett 12:4528–4531
Li YF, Zhou F, Forsyth CJ (2007) Gold(I)-catalyzed bis-spiroketalization: synthesis of the trioxadispiroketal-containing A-D rings of azaspiracid. Angew Chem Int Ed 46:279–282
Liu LP, Hammond GB (2010) Gold-catalyzed cascade annulations of 2-(ynol)aryl aldehydes: facile synthesis of benzochromanes and benzobicyclo[n.3.1]acetals. Org Lett 12:4640–4643
Tarselli MA, Zuccarello JL, Lee SJ, Gagné MR (2009) Gold(I)-catalyzed cascade cyclization of allenyl epoxides. Org Lett 11:3490–3492
Nguyen R-V, Yao X, Li C-J (2006) Highly efficient gold-catalyzed atom-economical annulation of phenols with dienes. Org Lett 8:2397–2399
Belting V, Krause N (2006) Gold-catalyzed tandem cycloisomerization-hydroalkoxylation of homopropargylic alcohols. Org Lett 8:4489–4492
Reddy MS, Kumar YK, Thirupathi N (2012) A new synthesis of gamma-butyrolactones via AuCl3- or Hg(II)-catalyzed intramolecular hydroalkoxylation o 4-bromo-3-yn-1ols. Org Lett 14:824–827
Alcaide B, Almendros P, del Campo TM, Carrascosa R (2010) Metal-catalyzed cycloisomerization and tandem oxycyclization/hydroxylation of alkynols: synthesis of nonfused, spiranic and fused oxabicyclic beta-Lactams. Eur J Org Chem 2010:4912–4919
Diéguez-Vázquez A, Tzschucke CC, Crecente-Campo J, McGrath S, Ley SV (2009) AuCl3-Catalyzed hydroalkoxylation of conjugated alkynoates: synthesis of five- and six-membered cyclic acetals. Eur J Org Chem 2009:1698–1706
Hashmi ASK, Buhrle M, Wolfle M, Rudolph M, Wieteck M, Rominger F, Frey W (2010) Gold catalysis: tandem reactions of diyne-diols and external nucleophiles as an easy access to tricyclic cage-like structures. Chem Eur J 16:9846–9854
Pennell MN, Foster RW, Turner PG, Hailes HC, Tame CJ, Sheppard TD (2014) Gold catalysed synthesis of 3-alkoxyfurans at room temperature. Chem Commun 50:1302–1304
Alcaide B, Almendros P, Carrascosa R, Torres MR (2010) Gold/acid-cocatalyzed regiodivergent preparation of bridged ketals via direct bis-oxycyclization of alkynic acetonides. Adv Synth Catal 352:1277–1283
Zhou L, Liu YZ, Zhang Y, Wang JB (2011) Sequential Au(I)-catalyzed reaction of water with o-acetylenyl-substituted phenyldiazoacetates. Beilstein J Org Chem 7:631–637
Belot S, Vogt KA, Besnard C, Krause N, Alexakis A (2009) Enantioselective one-pot organocatalytic Michael addition/gold-catalyzed tandem acetalization/cyclization. Angew Chem Int Ed 48:8923–8926
Tian GQ, Shi M (2007) Gold(I)-catalyzed additions of three-component 2-(arylmethylene)cyclopropylcarbinols, terminal arynes, and alcohols: an efficient access to 3-oxabicyclo[3.1.0]hexanes. Org Lett 9:4917–4920
Lu BL, Dai L, Shi M (2012) Strained small rings in gold-catalyzed rapid chemical transformations. Chem Soc Rev 41:3318–3339
Meng J, Zhao YL, Ren CQ, Li Y, Li Z, Liu Q (2009) Highly efficient access to bi- and tricyclic ketals through gold-catalyzed tandem reactions of 4-acyl-1,6-diynes. Chem Eur J 15:1830–1834
Handa S, Slaughter LM (2012) Enantioselective alkynylbenzaldehyde cyclizations catalyzed by chiral gold(I) acyclic diaminocarbene complexes containing weak Au–arene interactions. Angew Chem Int Ed 51:2912–2915
Wu H, He YP, Gong LZ (2013) Direct access to enantioenriched spiroacetals through asymmetric Relay catalytic three-component reaction. Org Lett 15:460–463
Cala L, Mendoza A, Fañanás FJ, Rodríguez F (2013) A catalytic multicomponent coupling reaction for the enantioselective synthesis of spiroacetals. Chem Commun 49:2715–2717
Jung HH, Floreancig PE (2007) Gold-catalyzed synthesis of oxygen- and nitrogen-containing heterocycles from alkynyl ethers: application to the total synthesis of andrachcinidine. J Org Chem 72:7359–7366
Barluenga J, Calleja J, Mendoza A, Rodríguez F, Fañanás FJ (2010) Synthesis of polycyclic compounds by a cascade cycloisomerisation/Diels-Alder reaction. Chem Eur J 16:7110–7112
Yao X, Li C-J (2006) Water-triggered and gold(I)-catalyzed cascade addition/cyclization of terminal alkynes with ortho-alkynylaryl aldehyde. Org Lett 8:1953–1955
Hopkinson MN, Gee AD, Gouverneur V (2011) Au(I) /Au(III) catalysis: an alternative approach for C-C oxidative coupling. Chem Eur J 17:8248–8262
Hashmi ASK, Blanco MC, Fischer D, Bats JW (2006) Gold catalysis: evidence for the in-situ reduction of gold(III) during the cyclization of allenyl carbinols. Eur J Org Chem 1387–1389
Wegner HA, Ahles S, Neuburger M (2008) A new gold-catalyzed domino cyclization and oxidative coupling reaction. Chem Eur J 14:11310–11313
Zhang R, Xu Q, Chen K, Gu P, Shi M (2013) Gold-catalyzed cascade oxidative cyclization and arylation of allenoates. Eur J Org Chem 2013:7366–7371
Ball LT, Green M, Lloyd-Jones GC, Russell CA (2010) Arylsilanes: application to gold-catalyzed oxyarylation of alkenes. Org Lett 12:4724–4727
Hopkinson MN, Ross JE, Giuffredi GT, Gee AD, Gouverneur V (2010) Gold-catalyzed cascade cyclization − oxidative alkynylation of allenoates. Org Lett 12:4904–4907
Hopkinson MN, Tessier A, Salisbury A, Giuffredi GT, Combettes LE, Gee AD, Gouverneur V (2010) Gold-catalyzed intramolecular oxidative cross-coupling of nonactivated arenes. Chem Eur J 16:4739–4743
Hashmi ASK, Lothschütz C, Döpp R, Rudolph M, Ramamurthi TD, Rominger F (2009) Gold and palladium combined for cross-coupling. Angew Chem Int Ed 48:8243–8246
Shi Y, Roth KE, Ramgren SD, Blum SA (2009) Catalyzed catalysis using carbophilic Lewis acidic gold and Lewis basic palladium: synthesis of substituted butenolides and isocoumarins. J Am Chem Soc 131:18022–18023
Zhang LM (2014) A non-diazo approach to alpha-oxo gold carbenes via gold-catalyzed alkyne oxidation. Acc Chem Res 47:877–888
Ye L, Cui L, Zhang G, Zhang L (2010) Alkynes as equivalents of α-diazo ketones in generating α-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones. J Am Chem Soc 132:3258–3259
Ye L, He W, Zhang L (2010) Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols. J Am Chem Soc 132:8550–8551
Wang Y, Ji K, Lan S, Zhang L (2012) Rapid access to chroman-3-ones through gold-catalyzed oxidation of propargyl aryl ethers. Angew Chem Int Ed 51:1915–1918
Yeom H-S, Shin S (2014) Catalytic access to alpha-oxo gold carbenes by n-o bond oxidants. Acc Chem Res 47:966–977
Shu C, Liu R, Liu S, Li J-Q, Yu Y-F, He Q, Lu X, Ye L-W (2015) Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy. Chem Asian J 10:91–95
Wang T, Shi S, Rudolph M, Hashmi ASK (2014) Synthesis of fully substituted 3-formyl-4-iodofurans via a gold(i)-catalyzed oxidation/1,2-alkynyl migration/cyclization/iodination cascade. Adv Synth Catal 356:2337–2342
Wang T, Huang L, Shi S, Rudolph M, Hashmi ASK (2014) Synthesis of highly substituted n-(furan-3-ylmethylene)benzenesulfonamides by a gold(i)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade. Chem Eur J 20:14868–14871
Wang T, Shi S, Hansmann MM, Rettenmeier E, Rudolph M, Hashmi ASK (2014) Synthesis of highly substituted 3-formylfurans by a gold(I)-catalyzed oxidation/1,2-alkynyl migration/cyclization cascade. Angew Chem Int Ed 53:3715–3719
Marion N, Nolan SP (2007) Propargylic esters in gold catalysis: access to diversity. Angew Chem Int Ed 46:2750–2752
Correa A, Marion N, Fensterbank L, Malacria M, Nolan SP, Cavallo L (2008) Golden carousel in catalysis: the cationic gold/propargylic ester cycle. Angew Chem Int Ed 47:718–721
Buzas A, Istrate F, Gagosz F (2006) Gold(I)-catalyzed stereoselective formation of functionalized 2,5-dihydrofurans. Org Lett 8:1957–1959
De Brabander JK, Liu B, Qian MX (2008) Au(I)- and Pt(II)-catalyzed cyclotherification of omega-hydroxy propargylic esters. Org Lett 10:2533–2536
Wang YM, Kuzniewski CN, Rauniyar V, Hoong C, Toste FD (2011) Chiral (acyclic diaminocarbene)gold(I)-catalyzed dynamic kinetic asymmetric transformation of propargyl esters. J Am Chem Soc 133:12972–12975
Kotikalapudi R, Swamy KCK (2013) Gold(I) catalysed cycloisomerisation of beta-hydroxy propargylic esters to dihydropyrans/2H-pyrans via allene intermediates. Tetrahedron 69:8002–8012
Uemura M, Watson IDG, Katsukawa M, Toste FD (2009) Gold(I)-catalyzed enantioselective synthesis of benzopyrans via rearrangement of allylic oxonium intermediates. J Am Chem Soc 131:3464–3465
Jiménez-Nuñez E, Claverie CK, Nieto-Oberhuber C, Echavarren AM (2006) Prins cyclizations in Au-catalyzed reactions of enynes. Angew Chem Int Ed 45:5452–5455
Molawi K, Delpont N, Echavarren AM (2010) Enantioselective synthesis of (-)-englerins A and B. Angew Chem Int Ed 49:3517–3519
Jiménez-Nuñez E, Molawi K, Echavarren AM (2009) Stereoselective gold-catalyzed cycloaddition of functionalized ketoenynes: synthesis of (+)-orientalol F. Chem Commun 7327–7329
Jiménez-Nuñez E, Raducan M, Lauterbach T, Molawi K, Solorio CR, Echavarren AM (2009) Evolution of propargyl ethers into allylgold cations in the cyclization of enynes. Angew Chem Int Ed 48:6152–6155
Shu X-Z, Liu X-Y, Ji K-G, Xiao H-Q, Liang Y-M (2008) Au-catalyzed tandem cyclization/[1,2]-alkyl migration reaction of epoxyalkynes: synthesis of spiropyranones. Chem Eur J 14:5282–5289
Lin GY, Li CW, Hung SH, Liu RS (2008) Diversity in gold- and silver-catalyzed cycloisomerization of epoxide-alkyne functionalities. Org Lett 10:5059–5062
Lin CC, Teng TM, Tsai CC, Liao HY, Liu RS (2008) Gold-catalyzed deoxygenative Nazarov cyclization of 2,4-dien-1-als for stereoselective synthesis of highly substituted cyclopentenes. J Am Chem Soc 130:16417–16423
Yang CY, Lin MS, Liao HH, Liu RS (2010) Diversity of products in the gold-catalyzed cyclization of 1-epoxy-1-alkynylcyclopropanes by using 1-oxyallyl cations. Chem Eur J 16:2696–2699
Liao HH, Liu RS (2011) Effects of haloniums on gold-catalyzed ring expansion of 1-oxiranyl-1-alkynylcyclopropanes. Chem Commun 47:1339–1341
Zhang XM, Tu YQ, Jiang YJ, Zhang YQ, Fan CA, Zhang FM (2009) Tandem reactions of cis-2-acyl-1-alkynyl-1-aryl cyclopropanes tuned by gold(I) and silver(I) catalysts: efficient synthesis of pyran-fused indene cores and 2,4,6-trisubstituted phenols. Chem Commun 4726–4728
Binder JT, Crone B, Kirsch SF, Liébert C, Menz H (2007) Synthesis of heterocyclic systems by transition-metal-catalyzed cyclization-migration reactions – a diversity-oriented strategy for the construction of spirocyclic 3(2H)-furanones and 3-pyrrolones. Eur J Org Chem 2007:1636–1647
Wegener M, Huber F, Bolli C, Jenne C, Kirsch SF (2015) Silver-free activation of ligated gold(I) chlorides: the use of [Me3NB12Cl11]- as a weakly coordinating anion in homogeneous gold catalysis. Chem Eur J 21:1328–1336
Crone B, Kirsch SF (2007) Synthesis of 4-iodo-3-furanones utilizing electrophile-induced tandem cyclization/1,2-migration reactions. J Org Chem 72:5435–5438
Zhang J, Schmalz HG (2006) Gold(I)-catalyzed reaction of 1-(1-alkynyl)-cyclopropyl ketones with nucleophiles: a modular entry to highly substituted furans. Angew Chem Int Ed 45:6704–6707
Fang R, Su CY, Zhao CY, Phillips DL (2009) DFT study on the mechanism and regioselectivity of gold(I)-catalyzed synthesis of highly substituted furans based on 1-(1-alkynyl)cyclopropyl ketones with nucleophiles. Organometallics 28:741–748
Li W, Yuan W, Pindi S, Shi M, Li GG (2010) Au/Ag-catalyzed intramolecular ring-opening of vinylidene-cyclopropanes (VDCPs): an easy Access to functional tetrahydropyrans. Org Lett 12:920–923
Peng B, Maulide N (2013) The redox-neutral approach to C-H functionalization. Chem Eur J 19:13274–13287
Jurberg ID, Odabachian Y, Gagosz F (2010) Hydroalkylation of alkynyl ethers via a gold(I)-catalyzed 1,5-hydride shift/cyclization sequence. J Am Chem Soc 132:3543–3552
Vadola PA, Sames D (2009) C-H bond functionalization via hydride transfer: direct coupling of unactivated alkynes and sp(3) C-H bonds catalyzed by platinum tetraiodide. J Am Chem Soc 131:16525–16528
Bolte B, Gagosz F (2011) Gold and brønsted acid catalyzed hydride shift onto allenes: divergence in product selectivity. J Am Chem Soc 133:7696–7699
López F, Mascareñas JL (2011) Recent developments in gold-catalyzed cycloaddition reactions. Beilstein J Org Chem 7:1075–1094
López F, Mascareñas JL (2013) Gold(I)-catalyzed enantioselective cycloaddition reactions. Beilstein J Org Chem 9:2250–2264
Garayalde D, Nevado C (2012) Gold-containing and gold-generated 1, n-dipoles as useful platforms toward cycloadditions and cyclizations. ACS Catal 2:1462–1479
Teng TM, Das A, Huple DB, Liu RS (2010) Gold-catalyzed stereoselective synthesis of 9-oxabicyclo[3.3.1]nona-4,7-dienes from diverse 1-oxo-4-oxy-5-ynes: a viable formal [4 + 2] cycloaddition on an s-trans-heterodiene framework. J Am Chem Soc 132:12565–12567
Teng TM, Liu RS (2010) Gold-catalyzed stereocontrolled oxacyclization/[4 + 2]-cycloaddition cascade of ketone-allene substrates. J Am Chem Soc 132:9298–9300
Zhang G, Zhang L (2008) Au-containing all-carbon 1,3-dipoles: generation and [3 + 2] cycloaddition reactions. J Am Chem Soc 130:12598–12599
Gao H, Wu X, Zhang J (2010) Exo/endo selectivity-control in Lewis-acid catalyzed tandem heterocyclization/formal [4 + 3] cycloaddition: synthesis of polyheterocycles from 2-(1-alkynyl)-2-alken-1-ones and 1,3-diphenylisobenzofuran. Chem Commun 46:8764–8766
Zhang G, Huang X, Li G, Zhang L (2008) Au-containing all-carbon 1,4-dipoles: generation and [4 + 2] annulation in the formation of carbo-/heterocycles. J Am Chem Soc 130:1814–1815
Escribano-Cuesta A, Lopez-Carrillo V, Janssen D, Echavarren AM (2009) Gold-catalyzed reactions of 1,5-and 1,6-enynes with carbonyl compounds: cycloaddition vs. metathesis. Chem Eur J 15:5646–5650
Schelwies M, Dempwolff AL, Rominger F, Helmchen G (2007) Gold-catalyzed intermolecular addition of carbonyl compounds to 1,6-enynes. Angew Chem Int Ed 46:5598–5601
Zhou Q, Chen X, Ma D (2010) Asymmetric, protecting-group-free total synthesis of (-)-englerin A. Angew Chem Int Ed 49:3513–3516
Obradors C, Echavarren AM (2013) Intermolecular gold-catalyzed cycloaddition of alkynes with oxoalkenes. Chem Eur J 19:3547–3551
Faustino H, Alonso I, Mascareñas JL, López F (2013) Gold(I)-catalyzed cascade cycloadditions between allenamides and carbonyl-tethered alkenes: an enantioselective approach to oxa-bridged medium-sized carbocycles. Angew Chem Int Ed 52:6526–6530
Faustino H, Varela I, Mascareñas JL, López F (2015) Gold(I)-catalyzed 2 + 2 + 2 cycloaddition of allenamides, alkenes and aldehydes: a straightforward approach to tetrahydropyrans. Chem Sci 6:2903–2908
Li CW, Lin GY, Liu RS (2010) Construction of 2,3-dihydrofuran cores through the [3 + 2] cycloaddition of gold alpha-carbonylcarbenoids with alkenes. Chem Eur J 16:5803–5811
Teng TM, Lin MS, Vasu D, Bhunia S, Liu TA, Liu RS (2010) Gold-catalyzed dealkoxylative carbocyclization/[3 + 3] annulation cascade of acetal-allene or ketal-allene substrates. Chem Eur J 16:4744–4748
Kramer S, Skrydstrup T (2012) Gold-catalyzed carbene transfer to alkynes: access to 2,4-disubstituted furans. Angew Chem Int Ed 51:4681–4684
Huang XL, Peng B, Luparia M, Gomes LFR, Veiros LF, Maulide N (2012) Gold-catalyzed synthesis of furans and furanones from sulfur ylides. Angew Chem Int Ed 51:8886–8890
Yeom H-S, Koo J, Park H-S, Wang Y, Liang Y, Yu Z-X, Shin S (2012) Gold-catalyzed intermolecular reactions of propiolic acids with alkenes: 4 + 2 annulation and enyne cross metathesis. J Am Chem Soc 134:208–211
Trillo B, López F, Montserrat S, Ujaque G, Castedo L, Lledós A, Mascareñas JL (2009) Gold-catalyzed [4C + 3C] intramolecular cycloaddition of allenedienes: synthetic potential and mechanistic implications. Chem Eur J 15:3336–3339
Gung BW, Craft DT (2009) Gold-catalyzed transannular [4 + 3] cycloaddition reactions. Tetrahedron Lett 50:2685–2687
Gung BW, Craft DT, Bailey LN, Kirschbaum K (2010) Gold-catalyzed transannular [4 + 3] cycloaddition reactions. Chem Eur J 16:639–644
Yang JM, Tang XY, Shi M (2015) Gold(I)-catalyzed intramolecular cycloisomerization of propargylic esters with furan rings. Chem Eur J 21:4534–4540
Alonso I, Trillo B, López F, Montserrat S, Ujaque G, Castedo L, Lledós A, Mascareñas JL (2009) Gold-catalyzed 4C + 2C cycloadditions of allenedienes, including an enantioselective version with New phosphoramidite-based catalysts: mechanistic aspects of the divergence between 4c + 3c and 4c + 2c pathways. J Am Chem Soc 131:13020–13030
Mauleón P, Zeldin RM, González AZ, Toste FD (2009) Ligand-controlled access to [4 + 2] and [4 + 3] cycloadditions in gold-catalyzed reactions of allene-dienes. J Am Chem Soc 131:6348–6349
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2016 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Mascareñas, J.L., López, F. (2016). Synthesis of Oxygenated Heterocyclic Compounds via Gold-Catalyzed Functionalization of π-Systems. In: Bandini, M. (eds) Au-Catalyzed Synthesis and Functionalization of Heterocycles. Topics in Heterocyclic Chemistry, vol 46. Springer, Cham. https://doi.org/10.1007/7081_2015_5006
Download citation
DOI: https://doi.org/10.1007/7081_2015_5006
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-35142-1
Online ISBN: 978-3-319-35144-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)