Abstract
Rhodium-catalyzed cyclocarbonylation reactions, which include the Pauson–Khand-type or [2+2+1] reactions, represent a powerful strategy for the synthesis of cyclic ketones through the combination of relatively simple unsaturated groups; namely, alkenes, alkynes, allenes, dienes, heterocumulenes, nitriles, and strained rings with carbon monoxide derived from either CO gas or through the decarbonylation of aldehydes. This chapter examines a variety of methods for the synthesis of carbo- and heterocyclic rings of different sizes, including diastereoselective and enantioselective approaches, and will also present the application of these reactions in the total synthesis of important natural products, as exemplified by (+)-asteriscanolide and (−)-ingenol.
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References
Davies HML, Sorensen EJ (eds) (2009) Chem Soc Rev 38:2969
Lautens M, Klute W, Tam W (1996) Chem Rev 96:49
Ojima I, Tzamarioudaki M, Li Z, Donovan RJ (1996) Chem Rev 96:635
Inglesby PA, Evans PA (2010) Chem Soc Rev 39:2791
Broere DLJ, Ruijter E (2012) Synthesis 44:2639
Reppe W, Schweckendiek WJ (1948) Liebigs Ann Chem 560:104
Khand IU, Knox GR, Pauson PL, Watts WE, Foreman MI (1973) J Chem Soc Perkin Trans 1 977
Strübing D, Beller M (2006) Top Organomet Chem 18:165
Pérez-Castells J (2006) Top Organomet Chem 19:207
Lee H-W, Kwong F-Y (2010) Eur J Org Chem 789
Shibata T (2011) In: De Vries JG, Molander GA, Evans PA (eds) Science of synthesis, vol 3. Thieme, Stuttgart, p 125
Lam FL, Lee HW, Wang J, Kwong FY (2012) Recent advancement of catalytic Pauson–Khand-type reactions. In: Rios Torres R (ed) The Pauson–Khand reaction: scope, variations and applications, 1st edn. Wiley, Chichester, pp 181–210
Heldeweg RF, Hogeveen H (1976) J Am Chem Soc 98:19
Chen J-R, Hu X-Q, Lu L-Q, Xiao W-J (2015) Chem Rev 115:5301
Murakami M, Itami K, Ito Y (1995) Angew Chem Int Ed 34:2691
Murakami M, Itami K, Ito Y (1996) J Am Chem Soc 118:11672
Murakami M, Itami K, Ito Y (1997) J Am Chem Soc 119:2950
Meng Q, Li M, Zhang J (2005) J Mol Struct Theochem 726:47
Murakami M, Itami K, Ito Y (1999) J Am Chem Soc 121:4130
Murakami M, Itami K, Ito Y (1999) Organometallics 18:1326
Mazumder S, Crandell DW, Lord RL, Baik M-H (2014) J Am Chem Soc 136:9414
Murakami M, Itami K, Ito Y (1998) Angew Chem Int Ed 37:3418
Zhang Y, Chen Z, Xiao Y, Zhang J (2009) Chem Eur J 15:5208
Wang T, Wang C-H, Zhang J (2011) Chem Commun 47:5578
Fukuyama T, Ohta Y, Brancour C, Miyagawa K, Ryu I, Dhimane A-L, Fensterbank L, Malacria M (2012) Chem Eur J 18:7243
Li X, Huang S, Schienebeck CM, Shu D, Tang W (2012) Org Lett 14:1584
Chen W, Tay J-H, Yu X-Q, Pu L (2012) J Org Chem 77:6215
Cho SH, Liebeskind LS (1987) J Org Chem 52:2631
Kurahashi T, de Meijere A (2005) Synlett 2619
Brancour C, Fukuyama T, Ohta Y, Ryu I, Dhimane A-L, Fensterbank L, Malacria M (2010) Chem Commun 46:5470
Schienebeck CM, Song W, Smits AM, Tang W (2015) Synthesis 47:1076
Shu D, Li X, Zhang M, Robichaux PJ, Tang W (2011) Angew Chem Int Ed 50:1346
Mauleón P, Krinsky JL, Toste FD (2009) J Am Chem Soc 131:4513
Garayalde D, Gómez-Bengoa E, Huang X, Goeke A, Nevado C (2010) J Am Chem Soc 132:4720
Wang S, Zhang L (2006) J Am Chem Soc 128:8414
Shu D, Li X, Zhang M, Robichaux PJ, Guzei IA, Tang W (2012) J Org Chem 77:6463
Li X, Song W, Tang W (2013) J Am Chem Soc 135:16797
Jiang G-J, Fu X-F, Li Q, Yu Z-X (2012) Org Lett 14:692
Wender PA, Deschamps NM, Sun R (2006) Angew Chem Int Ed 45:3957
Murakami M, Itami K, Ubukata M, Tsuji I, Ito Y (1998) J Org Chem 63:4
Yao Z-K, Li J, Yu Z-X (2011) Org Lett 13:134
Murakami M, Nishida S (1979) Chem Lett 927
Morizawa Y, Oshima K, Nozaki H (1982) Tetrahedron Lett 23:2871
Fu X-F, Xiang Y, Yu Z-X (2015) Chem Eur J 21:4242
Kobayashi T, Koga Y, Narasaka K (2001) J Organomet Chem 624:73
Jeong N, Sung BK, Kim JS, Park SB, Seo SD, Shin JY, In KY, Choi YK (2002) Pure Appl Chem 74:85
Koga Y, Kobayashi T, Narasaka K (1998) Chem Lett 249
Exon C, Magnus P (1983) J Am Chem Soc 105:2477
Jeong N, Lee S, Sung BK (1998) Organometallics 17:3642
Jeong N, Seo SD, Shin JY (2000) J Am Chem Soc 122:10220
Evans PA, Robinson JE (2001) J Am Chem Soc 123:4609
Ashfield BL, Miller KA, Martin SF (2004) Org Lett 6:1321
Ashfield BL, Miller KA, Smith AJ, Tran K, Martin SF (2005) Org Lett 7:1661
Fan L, Zhao W, Jiang W, Zhang J (2008) Chem Eur J 14:9139
Lee SI, Fukumoto Y, Chatani N (2010) Chem Commun 46:3345
Chen W, Tay J-H, Ying J, Yu X-Q, Pu L (2013) J Org Chem 78:2256
Ying J, Brown KB, Sandridge MJ, Hering BA, Sabat M, Pu L (2015) J Org Chem 80:3195
Wang H, Sawyer JR, Evans PA, Baik M-H (2008) Angew Chem Int Ed 47:342
Baik M-H, Mazumder S, Ricci P, Sawyer JR, Song Y-G, Wang H, Evans PA (2011) J Am Chem Soc 133:7621
Turlington M, Pu L (2011) Org Lett 13:4332
Jeong N, Sung BK, Choi YK (2000) J Am Chem Soc 122:6771
Kim DE, Choi C, Kim IS, Jeulin S, Ratovelomanana-Vidal V, Genêt J-P, Jeong N (2006) Synthesis 4053
Kim DE, Choi C, Kim IS, Jeulin S, Ratovelomanana-Vidal V, Genêt J-P, Jeong N (2007) Adv Synth Catal 349:1999
Kim DE, Ratovelomanana-Vidal V, Jeong N (2010) Adv Synth Catal 352:2032
Fan B-M, Xie J-H, Li S, Tu Y-Q, Zhou Q-L (2005) Adv Synth Catal 347:759
Cristóbal-Lecina E, Constantino AR, Grabulosa A, Riera A, Verdaguer X (2015) Organometallics 34:4989
Choi YH, Kwak J, Jeong N (2009) Tetrahedron Lett 50:6068
Kim DE, Park SH, Choi YH, Lee S-G, Moon D, Seo J, Jeong N (2011) Chem Asian J 6:2009
Jeong N, Kim DH, Choi JH (2004) Chem Commun 1134
Kim DE, Lee BH, Rajagopalasarma M, Genêt J-P, Ratovelomanana-Vidal V, Jeong N (2008) Adv Synth Catal 350:2695
Kim DE, Kwak J, Kim IS, Jeong N (2009) Adv Synth Catal 351:97
Suh WH, Choi M, Lee SI, Chung YK (2003) Synthesis 2169
Schmid TM, Consiglio G (2004) Chem Commun 2318
Kim DE, Kim IS, Ratovelomanana-Vidal V, Genêt J-P, Jeong N (2008) J Org Chem 73:7985
Chen G-Q, Shi M (2013) Chem Commun 49:698
Brummond KM, Sill PC, Rickards B, Geib SJ (2002) Tetrahedron Lett 43:3735
Brummond KM, Mitasev B (2004) Org Lett 6:2245
Brummond KM, Chen H, Fisher KD, Kerekes AD, Rickards B, Sill PC, Geib SJ (2002) Org Lett 4:1931
Manku S, Curran DP (2005) J Comb Chem 7:63
Mukai C, Nomura I, Yamanishi K, Hanaoka M (2002) Org Lett 4:1755
Mukai C, Nomura I, Kitagaki S (2003) J Org Chem 68:1376
Mukai C, Inagaki F, Yoshida T, Kitagaki S (2004) Tetrahedron Lett 45:4117
Mukai C, Inagaki F, Yoshida T, Yoshitani K, Hara Y, Kitagaki S (2005) J Org Chem 70:7159
Mukai C, Hirose T, Teramoto S, Kitagaki S (2005) Tetrahedron 61:10983
Inagaki F, Kawamura T, Mukai C (2007) Tetrahedron 63:5154
Brummond KM, Chen D (2008) Org Lett 10:705
Grillet F, Brummond KM (2013) J Org Chem 78:3737
Tap A, Lecourt C, Dhambri S, Arnould M, Galvani G, Nguyen van Buu O, Jouanneau M, Férézou J-P, Ardisson J, Lannou M-I, Sorin G (2016) Chem Eur J 22:4938
Makino T, Itoh K (2004) J Org Chem 69:395
Inagaki F, Mukai C (2006) Org Lett 8:1217
Inagaki F, Itoh N, Hayashi Y, Matsui Y, Mukai C (2011) Beilstein J Org Chem 7:404
Yuan W, Dong X, Shi M, McDowell P, Li G (2012) Org Lett 14:5582
Wender PA, Deschamps NM, Gamber GG (2003) Angew Chem Int Ed 42:1853
Croatt MP, Wender PA (2010) Eur J Org Chem 19
Wender PA, Croatt MP, Deschamps NM (2004) J Am Chem Soc 126:5948
Pitcock WH Jr, Lord RL, Baik M-H (2008) J Am Chem Soc 130:5821
Wender PA, Deschamps NM, Williams TJ (2004) Angew Chem Int Ed 43:3076
Brummond KM, Chen H, Mitasev B, Casarez AD (2004) Org Lett 6:2161
Wender PA, Croatt MP, Deschamps NM (2006) Angew Chem Int Ed 45:2459
Inagaki F, Narita S, Hasegawa T, Kitagaki S, Mukai C (2009) Angew Chem Int Ed 48:2007
Kawamura T, Inagaki F, Narita S, Takahashi Y, Hirata S, Kitagaki S, Mukai C (2010) Chem Eur J 16:5173
Shafawait MTS, Inagaki F, Kawamura T, Mukai C (2013) Tetrahedron 69:1509
Mukai C, Takahashi Y, Ogawa K, Hayashi Y, Inagaki F (2014) Chem Pharm Bull 62:84
Saito T, Sugizaki K, Otani T, Suyama T (2007) Org Lett 9:1239
Zhang Z, Xiao F, Huang B, Hu J, Fu B, Zhang Z (2016) Org Lett 18:908
Saito T, Furukawa N, Otani T (2010) Org Biomol Chem 8:1126
Saito T, Nihei H, Otani T, Suyama T, Furukawa N, Saito M (2008) Chem Commun 172
Iwata T, Inagaki F, Mukai C (2013) Angew Chem Int Ed 52:11138
Koga Y, Narasaka K (1999) Chem Lett 705
Lee SI, Park JH, Chung YK, Lee S-G (2004) J Am Chem Soc 126:2714
Jiao L, Lin M, Zhuo L-G, Yu Z-X (2010) Org Lett 12:2528
Lin M, Li F, Jiao L, Yu Z-X (2011) J Am Chem Soc 133:1690
Li C, Zhang H, Feng J, Zhang Y, Wang J (2010) Org Lett 12:3082
Zhao W, Zhang J (2011) Org Lett 13:688
Lu B-L, Wei Y, Shi M (2012) Organometallics 31:4601
Mazumder S, Shang D, Negru DE, Baik M-H, Evans PA (2012) J Am Chem Soc 134:20569
Shaw MH, Melikhova EY, Kloer DP, Whittingham WG, Bower JF (2013) J Am Chem Soc 135:4992
Shaw MH, Whittingham WG, Bower JF (2016) Tetrahedron 72:2731
Shaw MH, McCreanor NG, Whittingham WG, Bower JF (2015) J Am Chem Soc 137:463
Shaw MH, Croft RA, Whittingham WG, Bower JF (2015) J Am Chem Soc 137:8054
Kim S, Chung YK (2014) Org Lett 16:4352
Evans PA, Burnie AJ, Negru DE (2014) Org Lett 16:4356
Kim SY, Lee SI, Choi SY, Chung YK (2008) Angew Chem Int Ed 47:4914
Kim SY, Chung YK (2010) J Org Chem 75:1281
Wang Y, Yu Z-X (2015) Acc Chem Res 48:2288
Wender PA, Gamber GG, Hubbard RD, Zhang L (2002) J Am Chem Soc 124:2876
Wegner HA, de Meijere A, Wender PA (2005) J Am Chem Soc 127:6530
Wang Y, Wang J, Su J, Huang F, Jiao L, Liang Y, Yang D, Zhang S, Wender PA, Yu Z-X (2007) J Am Chem Soc 129:10060
Yu Z-X, Wender PA, Houk KN (2004) J Am Chem Soc 126:9154
Huang F, Yao Z-K, Wang Y, Wang Y, Zhang J, Yu Z-X (2010) Chem Asian J 5:1555
Bennacer B, Fujiwara M, Ojima I (2004) Org Lett 6:3589
Montero-Campillo MM, Rodríguez-Otero J, Cabaleiro-Lago E (2008) J Phys Chem A 112:2423
Bennacer B, Fujiwara M, Lee S-Y, Ojima I (2005) J Am Chem Soc 127:17756
Ojima I, Lee S-Y (2000) J Am Chem Soc 122:2385
Kaloko JJ, Teng Y-HG, Ojima I (2009) Chem Commun 4569
Huang Q, Hua R (2007) Chem Eur J 13:8333
Wender PA, Gamber GG, Hubbard RD, Pham SM, Zhang L (2005) J Am Chem Soc 127:2836
Morimoto T, Fuji K, Tsutsumi K, Kakiuchi K (2002) J Am Chem Soc 124:3806
Shibata T, Toshida N, Takagi K (2002) Org Lett 4:1619
Shibata T, Toshida N, Takagi K (2002) J Org Chem 67:7446
Fuji K, Morimoto T, Tsutsumi K, Kakiuchi K (2003) Angew Chem Int Ed 43:2409
Fuji K, Morimoto T, Tsutsumi K, Kakiuchi K (2004) Tetrahedron Lett 45:9163
Kwong FY, Li YM, Lam WH, Qiu L, Lee HW, Yeung CH, Chan KS, Chan ASC (2005) Chem Eur J 11:3872
Kwong FY, Lee HW, Qiu L, Lam WH, Li Y-M, Kwong HL, Chan ASC (2005) Adv Synth Catal 347:1750
Furusawa T, Morimoto T, Ikeda K, Tanimoto H, Nishiyama Y, Kakiuchi K, Jeong N (2015) Tetrahedron 71:875
Turlington M, Du Y, Ostrum SG, Santosh V, Wren K, Lin T, Sabat M, Pu L (2011) J Am Chem Soc 133:11780
Park JH, Cho Y, Chung YK (2010) Angew Chem Int Ed 49:5138
Ikeda K, Morimoto T, Kakiuchi K (2010) J Org Chem 75:6279
Ikeda K, Morimoto T, Tsumagari T, Tanimoto H, Nishiyama Y, Kakiuchi K (2012) Synlett 393
Lee HW, Chan ASC, Kwong FY (2007) Chem Commun 2633
Lee HW, Kwong FY, Chan ASC (2008) Synlett 1553
Lee HW, Lee LN, Chan ASC, Kwong FY (2008) Eur J Org Chem 3403
Park KH, Jung IG, Chung YK (2004) Org Lett 6:1183
Park KH, Chung YK (2005) Adv Synth Catal 347:854
Park JH, Kim SY, Kim SM, Lee SI, Chung YK (2007) Synlett 453
Park JH, Kim E, Kim H-M, Choi SY, Chung YK (2008) Chem Commun 2388
Sawano T, Thacker NC, Lin Z, McIsaac AR, Lin W (2015) J Am Chem Soc 137:12241
Van Ornum SG, Hoerner S, Cook JM (2012) Recent adventures with the Pauson–Khand reaction in total synthesis. In: Rios Torres R (ed) The Pauson–Khand reaction: scope, variations and applications, 1st edn. Wiley, Chichester, pp 211–238
Gehrtz PH, Hirschbeck V, Ciszek B, Fleischer I (2016) Synthesis 48:1573
Brady SF, Singh MP, Janso JE, Clardy J (2000) J Am Chem Soc 122:2116
Brummond KM, Gao D (2003) Org Lett 5:3491
Stork G, Danheiser RL (1973) J Org Chem 38:1775
Smith AB III, Dorsey BD, Ohba M, Lupo AT Jr, Malamas MS (1988) J Org Chem 53:4314
Kim DH, Kim K, Chung YK (2006) J Org Chem 71:8264
Hirose T, Miyakoshi N, Mukai C (2008) J Org Chem 73:1061
Jiao L, Yuan C, Yu Z-X (2008) J Am Chem Soc 130:4421
Fan X, Tang M-X, Zhuo L-G, Tu YQ, Yu Z-X (2009) Tetrahedron Lett 50:155
Fan X, Zhuo L-G, Tu YQ, Yu Z-X (2009) Tetrahedron 65:4709
Yuan C, Jiao L, Yu Z-X (2010) Tetrahedron Lett 51:5674
Hayashi Y, Miyakoshi N, Kitagaki S, Mukai C (2008) Org Lett 10:2385
Brummond KM, Chen D, Davis MM (2008) J Org Chem 73:5064
Oh D-C, Williams PG, Kauffman CA, Jensen PR, Fenical W (2006) Org Lett 8:1021
Aburano D, Inagaki F, Tomonaga S, Mukai C (2009) J Org Chem 74:5590
Datta S, Liu R-S (2005) Tetrahedron Lett 46:7985
Liang Y, Jiang X, Yu Z-X (2011) Chem Commun 47:6659
Liang Y, Jiang X, Fu X-F, Ye S, Wang T, Yuan J, Wang Y, Yu Z-X (2012) Chem Asian J 7:593
Frantz DE, Fässler R, Carreira EM (2000) J Am Chem Soc 122:1806
Jiang B, Chen Z, Xiong W (2002) Chem Commun 1524
Grillet F, Huang C, Brummond KM (2011) Org Lett 13:6304
Wen B, Hexum JK, Widen JC, Harki DA, Brummond KM (2013) Org Lett 14:2644
Tap A, Jouanneau M, Galvani G, Sorin G, Lannou M-I, Férézou J-P, Ardisson J (2012) Org Biomol Chem 10:8140
Wells SM, Brummond KM (2015) Tetrahedron Lett 56:3546
Hayashi Y, Ogawa K, Inagaki F, Mukai C (2012) Org Biomol Chem 10:4747
Zhang M, Tang W (2012) Org Lett 14:3756
Espino CG, Fiori KW, Kim M, Du Bois J (2004) J Am Chem Soc 126:15378
Jørgensen L, McKerrall SJ, Kuttruff CA, Ungeheuer F, Felding J, Baran PS (2013) Science 341:878
McKerrall SJ, Jørgensen L, Kuttruff CA, Ungeheuer F, Baran PS (2014) J Am Chem Soc 136:5799
Kawamura S, Chu H, Felding J, Baran PS (2016) Nature 532:90
Ying J, Pu L (2014) Chem Eur J 20:16301
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Burnie, A.J., Evans, P.A. (2017). Recent Developments in Rhodium-Catalyzed Cyclocarbonylation Reactions. In: Claver, C. (eds) Rhodium Catalysis. Topics in Organometallic Chemistry, vol 61. Springer, Cham. https://doi.org/10.1007/3418_2016_169
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