Abstract
In this review, we focus on synthetic applications of asymmetric transfer hydrogenation (ATH) of structurally complex ketone and imine substrates towards the synthesis of biologically active molecules and natural products with high levels of diastereo- and enantioselectivity. This approach should be interesting to a large scientific community from both academic and industrial assets, and specially life-science businesses. Commercial supply of catalysts is key for industrial groups aiming to implement this technology in their production campaigns. Thus, relevant examples of industrial use of ATH are described.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Notes
- 1.
While small-scale samples of ATH catalysts can be obtained by catalogue companies, Ru ATH catalysts figure prominently in the offer of large catalysts suppliers such as Johnson Matthey, Umicore, and Takasago.
References
Matsunami A, Kayaki Y (2018) Upgrading and expanding the scope of homogeneous transfer hydrogenation. Tetrahedron Lett 59:504–513
Milner L, Talavera G, Nedden HG (2017) Transfer hydrogenation catalysis of ketones and imines. Chim Oggi Chem Today 35:37–40
Stefane B, Pozgan F (2016) Metal-cataloxacarbazepineysed transfer hydrogenation of ketones. Top Curr Chem 374:14–50
Wills M (2016) Imino transfer hydrogenation reductions. Top Curr Chem 374:14–50
Echeverria P, Ayad T, Phansavath P, Ratovelomanana-Vidal V (2016) Recent developments in asymmetric hydrogenation and transfer hydrogenation of ketones and imines through dynamic kinetic resolution. Synthesis 48:2523–2539
Foubelo F, Yus M (2015) Catalytic asymmetric transfer hydrogenation of imines: recent advances. Chem Rec 15:907–924
Andrushko N, Andrushko V (2013) Asymmetric hydrogenation of C=O and C=N bonds in stereoselective synthesis. Stereoselective synthesis of drugs and natural products. Wiley, Weinheim, pp 909–959
Wang D, Astruc D (2015) The golden age of transfer hydrogenation. Chem Rev 115:6621–6686
Wang C, Villa-Marcos B, Xiao J (2011) Hydrogenation of imino bonds with half-sandwich metal catalysts. Chem Commun 47:9773–9785
He Y-M, Fan Q-H (2010) Phosphine-free chiral metal catalysts for highly effective asymmetric catalytic hydrogenation. Org Biomol Chem 8:2497–2504
Takehara J, Hashiguchi S, Fujii A, Inoue S, Ikariya T, Noyori R (1996) Amino alcohol effects on the ruthenium(II)-catalysed asymmetric transfer hydrogenation of ketones in propan-2-ol. Chem Commun 2:233–234
Hashiguchi S, Fujii A, Takehara J, Ikariya T, Noyori R (1995) Asymmetric transfer hydrogenation of aromatic ketones catalyzed by chiral ruthenium (II) complexes. J Am Chem Soc 117:7562–7563
Ikariya T, Blacker J (2007) Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts. Acc Chem Res 40:1300–1308
Morris DJ, Hayes AM, Wills M (2006) The “reverse-tethered” ruthenium (II) catalyst for asymmetric transfer hydrogenation: further applications. J Org Chem 71:7035–7044
Hodgkinson R, Jurčík V, Zanotti-Gerosa A, Nedden HG, Blackaby A, Clarkson GJ, Wills M (2014) Synthesis and catalytic applications of an extended range of tethered ruthenium(II)/η6-arene/diamine complexes. Organometallics 33:5517–5524
Cheung FK, Lin C, Minissi F, Lorente-Criville A, Graham M, Fox D, Wills M (2007) An investigation into the tether length and substitution pattern of arene-substituted complexes for asymmetric transfer hydrogenation ketones. Org Lett 9:4659–4662
Martins JED, Morris DJ, Tripathi B, Wills M (2008) Further ‘tethered’ Ru(II) catalysts for asymmetric transfer hydrogenation (ATH) of ketones; the use of a benzylic linker and a cyclohexyldiamine ligand. J Organomet Chem 693:3527–3532
Cheung FK, Clarke AJ, Clarkson GJ, Fox DJ, Graham MA, Lin C, Lorente-Criville A, Wills M (2010) Kinetic and structural studies on ‘tethered’ Ru(II) arene ketone reduction catalysts. Dalton Trans 39:1395–1402
Touge T, Hakamata T, Nara H, Kobayashi T, Sayo N, Saito T, Kayaki Y, Ikariya T (2011) Oxo-tethered ruthenium(II) complex as a bifunctional catalyst for asymmetric transfer hydrogenation and H2 hydrogenation. J Am Chem Soc 133:14960–14963
Parekh V, Ramsden A, Wills M (2011) Ether-tethered Ru(II)/TsDPEN complexes; synthesis and applications to asymmetric transfer hydrogenation. Cat Sci Technol 2:406–414
Kisic A, Stephan M, Mohar B (2014) ansa-Ruthenium(II) complexes of DPEN-SO2N(Me)(CH2)n(η6-aryl) conjugate ligands for asymmetric transfer hydrogenation of aryl ketones. Adv Synth Catal 356:3193–3198
Kisic A, Stephan M, Mohar B (2015) ansa-Ruthenium(II) complexes of R2NSO2DPEN-(CH2)n(η6-aryl) conjugate ligands for asymmetric transfer hydrogenation of aryl ketones. Adv Synth Catal 357:2540–2546
Cotman AE, Cahard D, Mohar B (2016) Stereoarrayed CF3-substituted 1,3-diols by dynamic kinetic resolution: ruthenium(II)-catalyzed asymmetric transfer hydrogenation. Angew Chem Int Ed 55:5294–5298
Matsunami A, Ikeda M, Nakamura H, Yoshida M, Kuwata S, Kayaki Y (2018) Accessible bifunctional oxy-tethered ruthenium(II) catalysts for asymmetric transfer hydrogenation. Org Lett 20:5213–5218
Hayes AM, Morris DJ, Clarkson GJ, Wills M (2005) A class of ruthenium (II) catalyst for asymmetric transfer hydrogenation of ketones. J Am Chem Soc 127:7318–7319
Hall AMR, Dong P, Codina A, Lowe JP, Hintermair U (2019) Kinetics of asymmetric transfer hydrogenation, catalyst deactivation, and inhibition with Noyori complexes as revealed by real-time high resolution FlowNMR spectroscopy. ACS Catal 9:2079–2090
Toubiana J, Medina L, Sasson Y (2014) The nature of the true catalyst in transfer hydrogenation with alcohol donors using (arene)2Ru2Cl4(II)/TsDPEN precursor. Mod Res Catal 3:68–88
Jolley KE, Zanotti-Gerosa A, Hancock F, Dyke A, Grainger DM, Medlock JA, Nedden HG, Le Paih JJM, Roseblade SJ, Seger A, Sivakumar V, Prokes I, Morris DJ, Wills M (2012) Hydrogenation of ketones and selective hydrogenation of aldehydes. Adv Synth Catal 2012:2545–2555
Soni R, Jolley KE, Gosiewska S, Clarkson GJ, Fang Z, Hall TH, Treloar BN, Knighton RC, Wills M (2018) Synthesis of enantiomerically pure and racemic benzyl-tethered Ru(II)/TsDPEN complexes by direct arene substitution: further complexes and applications. Organometallics 37:48–64
Touge T, Nara H, Fujiwhara M, Kayaki Y, Ikariya T (2016) Efficient access to chiral benzhydrols via asymmetric transfer hydrogenation of unsymmetrical benzophenones with bifunctional oxo-tethered ruthenium catalysts. J Am Chem Soc 138:10084–10087
Noyori R, Hashiguchi S (1997) Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes. Acc Chem Res 30(2):97–102
Rast S, Modec B, Stephan M, Mohar B (2016) γ-Sultam-cored N,N-ligands in the ruthenium(II)-catalyzed asymmetric transfer hydrogenation of aryl ketones. Org Biomol Chem 14:2112–2120
Dub PA, Gordon JC (2017) Metal–ligand bifunctional catalysis: the “accepted” mechanism, the issue of concertedness, and the function of the ligand in catalytic cycles involving hydrogen atoms. ACS Catal 7:6635–6655
Yamakawa M, Yamada I, Noyori R (2001) CH/π attraction: the origin of enantioselectivity in transfer hydrogenation of aromatic carbonyl compounds catalyzed by chiral η6-arene-ruthenium (II) complexes. Angew Chem Int Ed 40:2818–2821
Watanabe M, Murata K, Ikariya T (2002) Practical synthesis of optically active amino alcohols via asymmetric transfer hydrogenation of functionalized aromatic ketones. J Org Chem 67:1712–1715
Hamada T, Torii T, Onishi T, Izawa K, Ikariya T (2004) Asymmetric transfer hydrogenation of α-aminoalkyl α’-chloromethyl ketones with chiral Rh complexes. J Org Chem 69:7391–7394
Kosmalsky T, Wojtczak A, Zaidlewicz M (2009) Asymmetric synthesis of β-dialkylamino alcohols by transfer hydrogenation of α-dialkylamino ketones. Tetrahedron Asymmetry 20(10):1138–1143
Lu C, Luo Z, Huang L, Li X (2011) The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol. Tetrahedron Asymmetry 22(7):722–727
Liu J, Zhou D, Jia X, Huang L, Li X (2008) A convenient synthesis of (R)-samleterol via Rh-catalyzed asymmetric transfer hydrogenation. Tetrahedron Asymmetry 19(15):1824–1828
Huang L, Liu JSW, Liu BSA, Li X (2010) The asymmetric synthesis of (R,R)-formoterol via transfer hydrogenation with polyethylene glycol bound Rh catalyst in PEG 2000 and water. Chirality 22(2):206–211
Li L, Wu J, Wang F, Liao J, Zhang H, Lian C, Zhu J, Deng J (2007) Asymmetric transfer hydrogenation of ketones and imines with novel water-soluble chiral diamine as ligand in neat water. Green Chem 9:23–25
Komiyama M, Itoh T, Takeyasu T (2015) Scalable ruthenium-catalyzed asymmetric synthesis of a key intermediate for the β2-adrenergic receptor agonist. Org Process Res Dev 19:315–319
Merten J, Hennig A, Schwab P, Frohlich R, Tokalov SV, Gutzeit HO, Metz P (2006) A concise sultone route to highly oxygenated 1,10-seco-eudesmanolides-Enantioselective total synthesis of the antileukemic sesquiterpene lactones (−)-eriolanin and (−)-eriolangin. Eur J Org Chem 12(4):1144–1161
Lee D-M, Lee J-C, Jeong N, Lee K-I (2007) Asymmetric transfer hydrogenation of 2-tosyloxy-1-(4-hydroxyphenyl)ethanone derivatives: synthesis of (R)-tembamide, (R)-aegeline, (R)-octopamine and (R)-denopamine. Tetrahedron Asymmetry 18(22):2662–2667
Kwak SH, Lee D-M, Lee K-I (2009) Enantioselective Rh-catalyzed transfer hydrogenation of α-sulfonyloxy heteroaryl ketones: asymmetric synthesis of (S)-bufuralol. Tetrahedron Asymmetry 20(22):2639–2645
Zaidlewicz M, Tafelska-Kaczmarek A, Prewysz-Kwinto A (2005) Enantioselective reduction of benzofuryl halomethyl ketones: asymmetric synthesis of (R)-bufuralol. Tetrahedron Asymmetry 16(19):3205–3210
Grainger DM, Zanotti-Gerosa A, Cole KP, Mitchell D, May SA, Pollock PM, Calvin JR (2013) Development of a stepwise reductive deoxygenation process by Ru-catalysed homogeneous ketone reduction and Pd-catalysed hydrogenolysis in the presence of Cu salts. ChemCatChem 5:1205–1210
Zhang B, Xu M-H, Lin G-Q (2009) Catalytic enantioselective synthesis of chiral phthalides by efficient reductive cyclization of 2-acylarylcarboxylates under aqueous transfer hydrogenation conditions. Org Lett 11(20):4712–4715
Sterk D, Stephan MS, Mohar B (2004) Transfer hydrogenation of activated ketones using novel chiral Ru(II)-N-arenesulfonyl-1,2-diphenylethylenediamine complexes. Tetrahedron Lett 45:535–537
Learmonth DA, Grasa GA, Zanotti-Gerosa A (2007) Asymmetric catalytic reduction of oxcarbazepine. Patent WO 2007/012793 A1, 1 Feb 2007
Duan S, Li B, Dugger RW, Conway B, Kumar R, Martinez C, Makowski T, Pearson R, Olivier M, Colon-Cruz R (2017) Developing an asymmetric transfer hydrogenation process for (S)-5-fluoro-3-methylisobenzofuran-1(3H)-one, a key intermediate to lorlatinib. Org Process Res Dev 21:1340–1348
Hsin L-W, Chen C-W, Chang L-T (2005) Asymmetric total synthesis of (−)-octahydro-1H-benzofuro[3,2-e]isoquinoline, a partial structure of morphine. J Chin Chem Soc 52(2):339–346
Yamaguchi M, Park H, Hirama M (1997) Chemistry and antimicrobial activities of 3,5,7,9-decatetrayn-2-ol and related compounds. Chem Lett 26:535–536
Stang P, Diederich F (1995) Modern acetylene chemistry. Wiley-VCH, Weinheim
Fang Z, Wills M (2014) Asymmetric reduction of diynones and the total synthesis of (S)-panaxjapyne A. Org Lett 16:374–377
Fang Z, Wills M (2013) Asymmetric transfer hydrogenation of functionalized acetylenic ketones. J Org Chem 78(17):8594–8605
Figadere B, Harmange J-C, Laurens A, Cave A (1991) Stereospecific synthesis of (+)-muricatacin: a biologically active acetogenin derivative. Tetrahedron Lett 32(51):7539–7542
Kumaraswamy G, Ramakrishna D, Santhakumar K (2010) A concise enantioselective total synthesis of (+)-epi-muricatacin, using asymmetric hydrogenation/intramolecular iodoetherification as key steps. Tetrahedron Asymmetry 21(5):544–548
Kumaraswamy G, Padmaja M (2008) Enantioselective total synthesis of eicosanoid and its congener, using organocatalytic cyclopropanation and catalytic asymmetric transfer hydrogenation reactions as key steps. J Org Chem 73(13):5198–5201
Kumaraswamy G, Ramakrishna G, Sridhar B (2008) Enantioselective synthesis of cyclopropyl δ-lactonealdehydes and dodecyl-5-ene-1-yne-3-ol: advanced intermediates of sondelactone A and B. Tetrahedron Lett 52(15):1778–1782
Kumaraswamy G, Ramakrishna G, Naresh P, Jagadeesh B, Sridhar B (2009) A flexible enantioselective total synthesis of diospongins A and B and their enantiomers using catalytic hetero-Diels-Alder/Rh-catalyzed 1,4-addition and asymmetric transfer hydrogenation reactions as key steps. J Org Chem 74(21):8468–8471
Nonaka H, Maeda N, Kobayashi Y (2007) Improved synthesis of the polyhydroxylated central part of phoslactomycin B. Tetrahedron Lett 48(32):5601–5604
Kansal KK, Ahmad S, Mariappan S, Tyagi B, Perlman N, Le Paih J, Zanotti-Gerosa A (2007) Processes for the synthesis of azetidinone. Patent WO 2007/120824 A2, 25 Oct 2007
Remarchuk T, St-Jean F, Carrera D, Savage S, Yajima H, Wong B, Babu S, Deese A, Stults J, Dong MW, Askin D, Lane JW, Spencer KL (2014) Synthesis of Akt inhibitor ipatasertib. Part 2. Total synthesis and first kilogram scale-up. Org Process Res Dev 18:1652–1666
Crameri Y, Puntener K, Scalone M (2001) Process for the preparation of trans-(R,R)-actinol. Patent US6187961 B1, 13 Feb 2001
Uematsu N, Fujii A, Hashiguchi S, Ikariya T, Noyori R (1996) Asymmetric transfer hydrogenation of imines. J Am Chem Soc 118:4916–4917
Wu Z, Perez M, Scalone M, Ayad T, Ratovelomanana-Vidal V (2013) Ruthenium-catalyzed asymmetric transfer hydrogenation of 1-aryl-substituted dihydroisoquinolines: access to valuable chiral 1-aryl-tetrahydroisoquinoline scaffolds. Angew Chem Int Ed 52:4925–4928
Cheng J-J, Yang Y-S (2009) Enantioselective total synthesis of (−)-(S)-stepholidine. J Org Chem 74(23):9225–9228
Pyo MK, Lee D-H, Kim D-H, Lee J-H, Moon J-C, Chang KC, Yun-Choi HS (2008) Enantioselective synthesis of (R)-(+)- and (S)-(−)-higenamine and their analogues with effects on platelet aggregation and experimental animal model of disseminated intravascular coagulation. Bioorg Med Chem Lett 18(14):4110–4114
Czarnocki SJ, Wojtasiewicz K, Jozwiak AP, Maurin JK, Czarnocki Z, Drabowicz J (2008) Enantioselective synthesis of (+)-trypargine and (+)-crispine E. Tetrahedron 64(14):3176–3182
Parekh V, Ramsden JA, Wills M (2010) Asymmetric transfer hydrogenation of quinolines using tethered Ru (II) catalysts. Tetrahedron Asymmetry 21:1549–1556
Zhou Y-G (2007) Asymmetric hydrogenation of heteroaromatic compounds. Acc Chem Res 40(12):1357–1366
Tietze LF, Zhou Y, Topken E (2000) Synthesis of simple enantiopure tetrahydro-b-carbolines and tetrahydroisoquinolines. Eur J Org Chem 12:2247–2252
Santos LS, Pilli RA, Rawal VH (2004) Enantioselective total syntheses of (+)-arborescidine A, (−)-arborescidine B and (−)-arborescidine C. J Org Chem 69:1283–1289
Shankaraiah N, da Silva WA, Kleber C, Andrade Z, Santos LS (2008) Enantioselective total synthesis of (S)-(−)-quinolactacin B. Tetrahedron Lett 49:4289–4291
Shankaraiah N, Santos LS (2009) Enantioselective total synthesis of pyrroloquinolone as a potent PDE5 inhibitor. Tetrahedron Lett 50(5):520–523
Szawkalo J, Czarnocki SJ, Zawadzka A, Wojtasiewicz K, Leniewski A, Maurin JK, Czarnocki Z, Drabowicz J (2007) Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-b-carboline alkaloids. Tetrahedron Asymmetry 18(3):406–413
Szawkalo J, Zawadzka A, Wojtasiewicz K, Leniewski A, Drabowicz J, Czarnocki Z (2005) First enantioselective synthesis of the antitumour alkaloid (+)-crispine A and determination of its enantiomeric purity by 1H-NMR. Tetrahedron Asymmetry 16(22):3619–3621
Verzijl GKM, de Vries AHM, de Vries JG, Kapitan P, Dax T, Helms M, Nazir Z, Skranc W, Imboden C, Stichler J, Ward RA, Abele S, Lefort L (2013) Catalytic asymmetric reduction of a 3,4-dihydroisoquinoline for the large-scale production of almoxerant: hydrogenation or transfer hydrogenation? Org Process Res Dev 17:1531–1539
Mirabal-Gallardo Y, Pierola J, Shankaraiah N, Santos LS (2012) Enantioselective total synthesis of (S)-(+)-lennoxamine through asymmetric. Tetrahedron Lett 53:3672–3675
Strotman NA, Baxter CA, Brands KMJ, Cleator E, Krska SW, Reamer RA, Wallace DJ, Wright TJ (2011) Reaction development and mechanistic study of a ruthenium catalyzed intramolecular asymmetric reductive amination en route to the dual orexin inhibitor suvorexant (MK-4305). J Am Chem Soc 133:8362–8371
Roth P, Andersson PG, Somfai P (2002) Asymmetric reduction of azirines; a new route to chiral aziridines. Chem Commun 16:1752–1753
Chew RJ, Wills M (2018) Ruthenium-catalyzed asymmetric reduction of isoxazolium salts: access to optically active Δ4-isoxazolines. J Org Chem 83:2980–2985
Wu M, Cheng T, Ji M, Liu G (2015) Ru-catalyzed asymmetric transfer hydrogenation of α-trifluoromethylimines. J Org Chem 80:3708–3713
Dai X, Cahard D (2014) Enantioselective synthesis of α-trifluoromethyl arylmethylamines by ruthenium-catalyzed transfer hydrogenation reaction. Adv Synth Catal 356:1317–1328
Nobuyuki K, Yuichi K, Yoshitaka N (2006) 2,6-Dichloro-4-pyridylmethylamine derivative and agricultural or horticultural disease control agent. Patent WO 2006/004062 A1, 12 Jan 2006
Matsunaga H, Nakanishi K, Nakajima M, Kunieda T, Ishizuka T (2009) A chiral “roofed” cis-diamine-Ru(II) complex: an efficient catalyst for asymmetric transfer hydrogenation of ketimines. Heterocycles 78(3):617–622
Collados JF, Toledano E, Guijarro D, Yus M (2012) Microwave-assisted solvent-free synthesis of enantiomerically pure N-(tert-butylsulfinyl)imines. J Org Chem 77:5744–5750
Guijarro D, Pablo O, Yus M (2010) Asymmetric synthesis of chiral primary amines by transfer hydrogenation of N-(tert-butanesulfinyl)ketimines. J Org Chem 75(15):5265–5270
Denolf B, Mangelinckx S, Törnroos KW, De Kimpe N (2006) Use of α-chlorinated N-(tert-butanesulfinyl)imines in the synthesis of chiral aziridines. Org Lett 8:3129–3132
Guijarro D, Pablo O, Yus M (2009) Ruthenium-catalysed asymmetric transfer hydrogenation. Tetrahedron Lett 50:5386–5388
Guijarro D, Pablo O, Yus M (2011) Achiral β-amino alcohols as efficient ligands for the ruthenium-catalysed asymmetric transfer hydrogenation of sulfinylimines. Tetrahedron Lett 52:789–791
Pablo O, Guijarro D, Kovacs G, Lledos A, Ujaque G, Yus M (2012) A versatile Ru catalyst for the asymmetric transfer hydrogenation of both aromatic and aliphatic sulfinylimines. Chem Eur J 18:1969–1983
Pablo O, Guijarro D, Yus M (2014) Microwave-enhanced asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines. Eur J Org Chem 31:7034–7038
Guijarro D, Pablo O, Yus M (2013) Synthesis of highly enantiomerically enriched amines by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines. Org Synth 90:338–349
Pablo O, Guijarro D, Yus M (2013) Synthesis of nitrogenated heterocycles by asymmetric transfer. J Org Chem 78:9181
Guijarro D, Pablo O, Yus M (2013) Synthesis of γ-, δ-, and ε-lactams by asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)iminoesters. J Org Chem 78:3647–3654
Pablo O, Guijarro D, Yus M (2012) Chiral β-amino alcohols as ligands for the ruthenium-catalyzed asymmetric transfer hydrogenation of N-phosphinyl ketimines. Appl Sci 2:1–12
Blacker AJ, Martin J (2004) Scale-up studies in asymmetric transfer hydrogenation. Asymmetric catalysis on industrial scale: challenges, approaches and solutions. Wiley-VCH, Weinheim, pp 201–216
Williams GD, Pike RA, Wade CE, Wills M (2003) A one-pot process for the enantioselective synthesis of amines via reductive amination under transfer hydrogenation conditions. Org Lett 5:4227–4230
Williams GD, Wade CE, Wills M (2005) One-pot formation of nitrogen-containing heterocyclic ring systems using a deprotection–cyclisation–asymmetric reduction sequence. Chem Commun 37:4735–4737
Mangion IK, Chen C, Hongmei L, Maligres P, Chen Y, Christensen M, Cohen R, Jeon I, Klapars A, Krska S, Nguyen H, Reamer RA, Sherry BD, Zavialov I (2014) Enantioselective synthesis of an HCV NS5a antagonist. Org Lett 16(9):2310–2313
Xu F, Zacuto MJ, Kohmura Y, Rosen J, Gibb A, Alam M, Scott J, Tschaen D (2014) Asymmetric synthesis of highly functionalized tetrahydropyran DPP-4 inhibitor. Org Lett 16:5422–5425
Chung JYL, Scott JP, Anderson C, Bishop B, Bremeyer N, Cao Y, Chen Q, Dunn R, Kassim A, Lieberman D, Moment AJ, Sheen F, Zacuto MJ (2015) Evolution of a manufacturing route to omarigliptin, a long-acting DPP-4 inhibitor for the treatment of type 2 diabetes. Org Process Res Dev 19:1760–1768
Chen T, Ye Q, Zhao Q, Liu G (2015) Dynamic kinetic resolution of phthalides via asymmetric transfer hydrogenation: a strategy constructs 1,3-distereocentered 3-(2-hydroxy-2-arylethyl)isobenzofuran-1(3H)-one. Org Lett 17:4972–4975
Liu Z, Shultz CS, Sherwood CA, Krska S, Dormer PG, Desmond R, Lee C, Sherer EC, Shpungin J, Cuff J, Xu F (2011) Highly enantioselective synthesis of anti aryl β-hydroxy α-amino esters via DKR transfer hydrogenation. Tetrahedron Lett 52:1685–1688
Perez M, Echeverria PG, Martinez-Arripe E, Ez Zoubir M, Touati R, Zhang Z, Genet JP, Phansavath P, Ayad T, Ratovelomanana-Vidal V (2015) An efficient stereoselective total synthesis of all stereoisomers of the antibiotic thiamphenicol through ruthenium-catalyzed asymmetric reduction by dynamic kinetic resolution. Eur J Org Chem 2015:5949–5958
Seashore-Ludlow B, Saint-Dizier F, Somfai P (2012) Asymmetric transfer hydrogenation coupled with dynamic kinetic resolution in water: synthesis of anti-β-hydroxy-α-amino acid derivatives. Org Lett 14:6334–6337
Seashore-Ludlow B, Villo P, Somfai P (2012) Enantioselective synthesis of anti-β-hydroxy-α-amido esters by asymmetric transfer hydrogenation in emulsions. Chem Eur J 18:7219–7223
Seashore-Ludlow B, Villo P, Hacker C, Somfai P (2010) Enantioselective synthesis of anti-hydroxy-α-amido esters via transfer hydrogenation. Org Lett 12:5274–5277
Echeverria PG, Cornil J, Ferard C, Guerinot A, Cossy J, Phansavath P, Ratovelomanana-Vidal V (2015) Asymmetric transfer hydrogenation of α-amino β-keto ester hydrochlorides through dynamic kinetic resolution. RSC Adv 5:56815–56819
Bai J, Miao S, Wu Y, Zhang Y (2011) Asymmetric reduction of 2-chloro-3-oxo esters by transfer hydrogenation. Chin J Chem 29:2476–2480
Monnereau L, Cartigny D, Scalone M, Ayad T, Ratovelomanana-Vidal V (2015) Efficient synthesis of differentiated syn-1,2-diol derivatives by asymmetric transfer hydrogenation–dynamic kinetic resolution of α-alkoxy-substituted β-ketoesters. Chem Eur J 21:11799–11806
Bromhead LJ, Visser J, McErlean CSP (2014) Enantioselective synthesis of the strigolactone mimic (+)-GR24. J Org Chem 79:1516–1520
Wu Y, Geng Z, Bai J, Zhang Y (2011) Synthesis of chiral 2-aroyl-1-tetralols: asymmetric transfer hydrogenation of 2-aroyl-1-tetralones via dynamic kinetic resolution. Chin J Chem 29:1467–1472
Kumaraswamy G, Narayanarao V, Shanigaram P (2015) Diastereoselective synthesis of an advanced intermediate of the crocacin family using asymmetric transfer hydrogenation-DKR and Marshall allenylation as key reactions. Tetrahedron 71:8960–8964
Kumaraswamy G, Narayana MA, Narayanarao V, Vemulapalli SPB, Bharatam J (2013) Enantioselective synthesis of δ-/γ-alkoxy-β-hydroxy-α-alkyl-substituted Weinreb amides via DKR–ATH: application to the synthesis of advanced intermediate of (−)-brevisamide. Org Biomol Chem 11:6751–6765
Son S-M, Lee H-K (2013) Dynamic kinetic resolution-based asymmetric transfer hydrogenation of 2-benzoylmorpholinones and its use in concise stereoselective synthesis of all four stereoisomers of the antidepressant reboxetine. J Org Chem 78:8396–8404
Steward KM, Gentry EC, Johnson JS (2012) Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation. J Am Chem Soc 134:7329–7332
Steward KM, Corbett MT, Goodman CG, Johnson JS (2012) Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of α-keto esters. J Am Chem Soc 134:20197–20206
Goodman CG, Do DT, Johnson JS (2013) Asymmetric synthesis of anti-β-amino-α-hydroxy esters via dynamic kinetic resolution of β-amino-α-keto esters. Org Lett 15:2446–2449
Villacrez M, Somfai P (2013) Enantioselective synthesis of anti-β-amido-α-hydroxy esters via asymmetric transfer hydrogenation coupled with dynamic kinetic resolution. Tetrahedron Lett 54:5266–5268
Son S-M, Lee H-K (2014) Dynamic kinetic resolution based asymmetric transfer hydrogenation of α-alkoxy-β-ketophosphonates. Diastereo- and enantioselective synthesis of monoprotected 1,2-dihydroxyphosphonates. J Org Chem 79:2666–2681
Corbett MT, Johnson JS (2013) Diametric stereocontrol in dynamic catalytic reduction of racemic acyl phosphonates: divergence from α-keto ester congeners. J Am Chem Soc 135:594–597
Gen Z, Wu Y, Miao S, Shen Z, Zhang Y (2011) Highly enantioselective synthesis of β-hydroxysulfonamides by asymmetric transfer hydrogenation. Tetrahedron Lett 52:907–909
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2019 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Talavera, G., Santana Fariña, A., Zanotti-Gerosa, A., Nedden, H.G. (2019). Structural Diversity in Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation Reactions. In: Colacot, T., Sivakumar, V. (eds) Organometallics in Process Chemistry. Topics in Organometallic Chemistry, vol 65. Springer, Cham. https://doi.org/10.1007/3418_2019_27
Download citation
DOI: https://doi.org/10.1007/3418_2019_27
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-27960-8
Online ISBN: 978-3-030-27961-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)