Abstract
Transition metal-catalyzed enantioselective hydrogenation of enamides and enamines is one of the most important methods for the preparation of optically active amines. This review describes the recent developments of highly efficient catalytic asymmetric hydrogenation of enamides, and enamines. It specifically focuses on the substrates because hydrogenation of enamides and enamines is highly dependent on the substrates although the chiral metal catalysts play a significant role.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Kagan HB, Dang TP (1972) J Am Chem Soc 94:6429
de Vries JG, Elsevier CJ (2007) The handbook of homogeneous hydrogenation. Wiley VCH, Weinheim
Nugent TC, El-Shazly M (2010) Adv Synth Catal 352:753
Xie JH, Zhou QL (2012) Acta Chim Sinica 70:1427
Lee NE, Buchwald SL (1994) J Am Chem Soc 116:5985
Tararov VI, Kadyrov R, Riermeier TH, Holz J, Börner A (2000) Tetrahedron Lett 41:2351
Ohta T, Ikegami H, Miyake T, Takaya H (1995) J Organometal Chem 502:169
Becalski AG, Cullen WR, Fryzuk MD, James BR, Kang GJ, Retting SJ (1991) Inorg Chem 30:5002
Guo HC, Ding KL, Dai LX (2004) Chin Sci Bull 49:1575
Xie JH, Zhu SF, Zhou QL (2012) Chem Soc Rev 41:4126
Blaser HU, Spindler F, Thommen M (2007) In: de Vries JG, Elsevier CJ (eds) The handbook of homogeneous hydrogenation. Wiley VCH, Weinheim, p 1279
Burk MJ, Wang YM, Lee JR (1996) J Am Chem Soc 118:5142
Li W, Zhang Z, Xiao D, Zhang X (2000) J Org Chem 65:3489
Xiao D, Zhang Z, Zhang X (1999) Org Lett 1:1679
Yan Y, Zhang X (2006) Tetrahedron Lett 47:1567
Li W, Zhang X (2000) J Org Chem 65:5871
Yan YY, RajanBabu TV (2000) Org Lett 2:4137
Lee SG, Zhang YJ, Song CE, Lee JK, Choi JH (2002) Angew Chem Int Ed 41:847
Zhang FY, Pai CC, Chan ASC (1998) J Am Chem Soc 120:5808
Zhou YG, Zhang X (2002) Chem Commun 1124
Wang CJ, Gao F, Liang G (2008) Org Lett 10:4711
Hu XP, Zheng Z (2004) Org Lett 6:3585
Zeng QH, Hu XP, Duan ZC, Liang XM, Zheng Z (2005) Tetrahedron Asymmetry 16:1233
Li X, Jia X, Xu L, Kok SHL, Yip CW, Chan ASC (2005) Adv Synth Catal 347:1904
Huang JD, Hu XP, Duan ZC, Zeng QH, Yu SB, Deng J, Wang DY, Zheng Z (2006) Org Lett 8:4367
Qiu M, Hu XP, Wang DY, Deng J, Huang JD, Yu SB, Duan ZC, Zheng Z (2008) Adv Synth Catal 350:1413
Tang W, Zhang X (2001) Angew Chem Int Ed 41:1612
Imamoto T, Oohara N, Takahashi H (2004) Synthesis 1353
Tang W, Qu B, Capacci AG, Rodriguez S, Wei X, Haddad N, Narayanan B, Ma S, Grinberg N, Yee NK, Krishnamurthy D, Senanayake CH (2010) Org Lett 12:176
Imamoto T, Tamura K, Zhang Z, Horiuchi Y, Sugiya M, Yoshida K, Yanagisawa A, Gridnev ID (2012) J Am Chem Soc 134:1754
Zhang Z, Tamura K, Mayama D, Sugiya M, Imamoto T (2012) J Org Chem 77:4184
Stephan M, Šterk D, Mohar B (2009) Adv Synth Catal 351:2779
Zupančič B, Mohar B, Stephan M (2010) Org Lett 12:1296
Zupančič B, Mohar B, Stephan M (2010) Org Lett 12:3022
Stephan M, Šterk D, Zupančič B, Mohar B (2011) Org Biomol Chem 9:5266
Hu AG, Fu Y, Xie JH, Zhou H, Wang LX, Zhou QL (2002) Angew Chem Int Ed 41:2348
Jia X, Guo R, Li X, Yao X, Chan ASC (2002) Tetrahedron Lett 43:5541
Jia X, Li X, Xu L, Shi Q, Yao X, Chan ASC (2003) J Org Chem 68:4539
Bernsman H, van den Berg M, Hoen R, Minnaard AJ, Mehler G, Reetz MT, de Vries JG, Feringa BL (2005) J Org Chem 70:943
Li X, Jia X, Lu G, AuYeung TTL, Lam KHT, Lo WH, Chan ASC (2003) Tetrahedron Asymmetry 14:2687
Zeng QH, Hu XP, Duan ZC, Liang XM, Zheng Z (2006) J Org Chem 71:393
Liu Y, Ding K (2005) J Am Chem Soc 127:10488
Zhao B, Wang Z, Ding K (2006) Adv Synth Catal 348:1049
Reetz MT, Mehler G, Meiswinkel A, Sell T (2002) Tetrahedron Lett 43:7941
Huang H, Zheng Z, Luo H, Bai C, Hu X, Chen H (2003) Org Lett 5:4137
Huang H, Zheng Z, Luo H, Bai C, Hu X, Chen H (2004) J Org Chem 69:2355
Pignataro L, Boghi M, Civera M, Carboni S, Piarulli U, Gennari C (2012) Chem Eur J 18:1383
Pignataro L, Bovio C, Civera M, Piarulli U, Gennari C (2012) Chem Eur J 18:10368
Hu XP, Huang JD, Zeng QH, Zheng Z (2006) Chem Commun 293
Chen W, Roberts SN, Whittall J (2006) Tetrahedron Lett 47:4263
Zhao Y, Huang H, Shao J, Xia C (2011) Tetrahedron Asymmetry 22:769
Wang X, Ding K (2004) J Am Chem Soc 126:10524
Zhang F, Li Y, Li ZW, He YM, Zhu SF, Fan QH, Zhou QL (2008) Chem Commun 6048
Shi L, Wang X, Sandoval CA, Li M, Qi Q, Li Z, Ding K (2006) Angew Chem Int Ed 45:4108
Zhang W, Zhang X (2006) Angew Chem Int Ed 45:5515
Wang T, Lamb ML, Scott DA et al (2008) J Med Chem 51:4672
O’Shea PD, Gauvreau D, Gosselin F, Hughes G, Nadeau C, Roy A, Shultz CS (2009) J Org Chem 74:4547
Lefort L, Boogers JAF, Kuilman T, Vijn RJ, Janssen J, Straatman H, de Vries JG, de Vries AHM (2010) Org Process Res Dev 14:568
Gridnev ID, Yasutake M, Higashi N, Imamoto T (2001) J Am Chem Soc 123:5268
Gridnev ID, Imamoto T, Hoge G, Kouchi M, Takahashi H (2008) J Am Chem Soc 130:2560
Enthaler S, Erre G, Junge K, Addis D, Kadyrov R, Beller M (2008) Chem Asian J 3:1104
Allwein SP, McWilliams JC, Secord EA, Mowrey DR, Nelson TD, Kress MH (2006) Tetrahedron Lett 47:6409
Yang Q, Gao W, Deng J, Zhang X (2006) Tetrahedron Lett 47:821
Li W, Waldkirich JP, Zhang X (2002) J Org Chem 67:7618
Chi Y, Zhang X (2002) Tetrahedron Lett 43:4849
Hoen R, van den Berg M, Bernsmann H, Minnaard AJ, de Vries JG, Feringa BL (2004) Org Lett 6:1433
Huang H, Liu X, Chen H, Zheng Z (2005) Tetrahedron Asymmetry 16:693
Storace L, Anzalone L, Confalone PN et al (2002) Org Proc Res Dev 6:54
Zhu G, Casalnuovo AL, Zhang X (1998) J Org Chem 63:8100
Chen J, Zhang W, Geng H, Li W, Hou G, Lei A, Zhang X (2009) Angew Chem Int Ed 48:800
Zhu SF, Liu T, Yang S, Song S, Zhou QL (2012) Tetrahedron 68:7685
Wallace DJ, Campos KR, Shultz CS, Klapars A, Zewge D, Crump BR, Phenix BD, McWilliams JC, Krska S, Sun Y, Chen CY, Spindler F (2009) Org Proc Res Dev 13:84
Tang W, Chi Y, Zhang X (2002) Org Lett 4:1695
Fu Y, Guo XX, Zhu SF, Hu AG, Xie JH, Zhou QL (2004) J Org Chem 69:4648
Renaud JL, Dupau P, Hay AE, Guingouain M, Dixneuf PH, Bruneau C (2003) Adv Synth Catal 345:230
Jiang XB, Lefort L, Goudriaan PE, de Vires AHM, van Leeuwen PWNM, de Vries JG, Reek JNH (2006) Angew Chem Int Ed 45:1223
Wu Z, Ayad T, Ratovelomenana-Vidal V (2011) Org Lett 13:3782
Beliaev A, Wahnon J, Russo D (2012) Org Proc Res Dev 16:704
Lennon IC, Ramsden JA, Brear CJ, Broady SD, Muir JC (2007) Tetrahedron Lett 48:4623
Zhang Z, Zhu G, Jiang Q, Xiao D, Zhang X (1999) J Org Chem 64:1774
Dupau P, Bruneau C, Dixneuf PH (2001) Adv Synth Catal 343:331
Patureau FW, de Boer S, Kuil M, Meeuwissen J, Breuil PAR, Siegler MA, Spek AL, Sandee AJ, de Bruin B, Reek JNH (2009) J Am Chem Soc 131:6683
Stumpf A, Reynolds M, Sutherlin D, Babu S, Bappert E, Spindler F, Welch M, Gaudino J (2011) Adv Synth Catal 353:3367
Noyori R, Ohta M, Hsiao Y, Kitamura M, Ohta T, Takaya H (1986) J Am Chem Soc 108:7117
Zhou YG, Yang PY, Han XW (2005) J Org Chem 70:1679
Cheruku P, Church TL, Trifonova A, Wartmann T, Andersson PG (2008) Tetrahedron Lett 49:7290
Baeza A, Pfaltz A (2009) Chem Eur J 15:2266
Yan PC, Xie JH, Zhou QL (2010) Chin J Chem 28:1736
Hou GH, Xie JH, Wang LX, Zhou QL (2006) J Am Chem Soc 128:11774
Hou GH, Xie JH, Yan PC, Zhou QL (2009) J Am Chem Soc 131:1366
Yan PC, Xie JH, Hou GH, Wang LX, Zhou QL (2009) Adv Synth Catal 351:3243
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2013 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Zhou, QL., Xie, JH. (2013). Transition Metal-Catalyzed Enantioselective Hydrogenation of Enamides and Enamines. In: Li, W., Zhang, X. (eds) Stereoselective Formation of Amines. Topics in Current Chemistry, vol 343. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2013_482
Download citation
DOI: https://doi.org/10.1007/128_2013_482
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-53928-2
Online ISBN: 978-3-642-53929-9
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)