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2014 | OriginalPaper | Chapter

Transition Metal-Catalyzed Enantioselective Hydrogenation of Enamides and Enamines

Authors : Qi-Lin Zhou, Jian-Hua Xie

Published in: Stereoselective Formation of Amines

Publisher: Springer Berlin Heidelberg

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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.

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Literature
2.
go back to reference de Vries JG, Elsevier CJ (2007) The handbook of homogeneous hydrogenation. Wiley VCH, Weinheim de Vries JG, Elsevier CJ (2007) The handbook of homogeneous hydrogenation. Wiley VCH, Weinheim
6.
go back to reference Tararov VI, Kadyrov R, Riermeier TH, Holz J, Börner A (2000) Tetrahedron Lett 41:2351CrossRef Tararov VI, Kadyrov R, Riermeier TH, Holz J, Börner A (2000) Tetrahedron Lett 41:2351CrossRef
7.
8.
go back to reference Becalski AG, Cullen WR, Fryzuk MD, James BR, Kang GJ, Retting SJ (1991) Inorg Chem 30:5002CrossRef Becalski AG, Cullen WR, Fryzuk MD, James BR, Kang GJ, Retting SJ (1991) Inorg Chem 30:5002CrossRef
9.
go back to reference Guo HC, Ding KL, Dai LX (2004) Chin Sci Bull 49:1575 Guo HC, Ding KL, Dai LX (2004) Chin Sci Bull 49:1575
11.
go back to reference Blaser HU, Spindler F, Thommen M (2007) In: de Vries JG, Elsevier CJ (eds) The handbook of homogeneous hydrogenation. Wiley VCH, Weinheim, p 1279 Blaser HU, Spindler F, Thommen M (2007) In: de Vries JG, Elsevier CJ (eds) The handbook of homogeneous hydrogenation. Wiley VCH, Weinheim, p 1279
18.
20.
23.
go back to reference Zeng QH, Hu XP, Duan ZC, Liang XM, Zheng Z (2005) Tetrahedron Asymmetry 16:1233CrossRef Zeng QH, Hu XP, Duan ZC, Liang XM, Zheng Z (2005) Tetrahedron Asymmetry 16:1233CrossRef
24.
go back to reference Li X, Jia X, Xu L, Kok SHL, Yip CW, Chan ASC (2005) Adv Synth Catal 347:1904CrossRef Li X, Jia X, Xu L, Kok SHL, Yip CW, Chan ASC (2005) Adv Synth Catal 347:1904CrossRef
25.
go back to reference Huang JD, Hu XP, Duan ZC, Zeng QH, Yu SB, Deng J, Wang DY, Zheng Z (2006) Org Lett 8:4367CrossRef Huang JD, Hu XP, Duan ZC, Zeng QH, Yu SB, Deng J, Wang DY, Zheng Z (2006) Org Lett 8:4367CrossRef
26.
go back to reference Qiu M, Hu XP, Wang DY, Deng J, Huang JD, Yu SB, Duan ZC, Zheng Z (2008) Adv Synth Catal 350:1413CrossRef Qiu M, Hu XP, Wang DY, Deng J, Huang JD, Yu SB, Duan ZC, Zheng Z (2008) Adv Synth Catal 350:1413CrossRef
28.
go back to reference Imamoto T, Oohara N, Takahashi H (2004) Synthesis 1353 Imamoto T, Oohara N, Takahashi H (2004) Synthesis 1353
29.
go back to reference 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 12:176CrossRef 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 12:176CrossRef
30.
go back to reference Imamoto T, Tamura K, Zhang Z, Horiuchi Y, Sugiya M, Yoshida K, Yanagisawa A, Gridnev ID (2012) J Am Chem Soc 134:1754CrossRef Imamoto T, Tamura K, Zhang Z, Horiuchi Y, Sugiya M, Yoshida K, Yanagisawa A, Gridnev ID (2012) J Am Chem Soc 134:1754CrossRef
31.
35.
36.
go back to reference Hu AG, Fu Y, Xie JH, Zhou H, Wang LX, Zhou QL (2002) Angew Chem Int Ed 41:2348CrossRef Hu AG, Fu Y, Xie JH, Zhou H, Wang LX, Zhou QL (2002) Angew Chem Int Ed 41:2348CrossRef
37.
38.
39.
go back to reference Bernsman H, van den Berg M, Hoen R, Minnaard AJ, Mehler G, Reetz MT, de Vries JG, Feringa BL (2005) J Org Chem 70:943CrossRef Bernsman H, van den Berg M, Hoen R, Minnaard AJ, Mehler G, Reetz MT, de Vries JG, Feringa BL (2005) J Org Chem 70:943CrossRef
40.
go back to reference Li X, Jia X, Lu G, AuYeung TTL, Lam KHT, Lo WH, Chan ASC (2003) Tetrahedron Asymmetry 14:2687CrossRef Li X, Jia X, Lu G, AuYeung TTL, Lam KHT, Lo WH, Chan ASC (2003) Tetrahedron Asymmetry 14:2687CrossRef
41.
44.
45.
46.
47.
go back to reference Pignataro L, Boghi M, Civera M, Carboni S, Piarulli U, Gennari C (2012) Chem Eur J 18:1383CrossRef Pignataro L, Boghi M, Civera M, Carboni S, Piarulli U, Gennari C (2012) Chem Eur J 18:1383CrossRef
48.
go back to reference Pignataro L, Bovio C, Civera M, Piarulli U, Gennari C (2012) Chem Eur J 18:10368CrossRef Pignataro L, Bovio C, Civera M, Piarulli U, Gennari C (2012) Chem Eur J 18:10368CrossRef
49.
go back to reference Hu XP, Huang JD, Zeng QH, Zheng Z (2006) Chem Commun 293 Hu XP, Huang JD, Zeng QH, Zheng Z (2006) Chem Commun 293
51.
53.
go back to reference Zhang F, Li Y, Li ZW, He YM, Zhu SF, Fan QH, Zhou QL (2008) Chem Commun 6048 Zhang F, Li Y, Li ZW, He YM, Zhu SF, Fan QH, Zhou QL (2008) Chem Commun 6048
54.
go back to reference Shi L, Wang X, Sandoval CA, Li M, Qi Q, Li Z, Ding K (2006) Angew Chem Int Ed 45:4108CrossRef Shi L, Wang X, Sandoval CA, Li M, Qi Q, Li Z, Ding K (2006) Angew Chem Int Ed 45:4108CrossRef
57.
go back to reference O’Shea PD, Gauvreau D, Gosselin F, Hughes G, Nadeau C, Roy A, Shultz CS (2009) J Org Chem 74:4547CrossRef O’Shea PD, Gauvreau D, Gosselin F, Hughes G, Nadeau C, Roy A, Shultz CS (2009) J Org Chem 74:4547CrossRef
58.
go back to reference Lefort L, Boogers JAF, Kuilman T, Vijn RJ, Janssen J, Straatman H, de Vries JG, de Vries AHM (2010) Org Process Res Dev 14:568CrossRef Lefort L, Boogers JAF, Kuilman T, Vijn RJ, Janssen J, Straatman H, de Vries JG, de Vries AHM (2010) Org Process Res Dev 14:568CrossRef
59.
60.
go back to reference Gridnev ID, Imamoto T, Hoge G, Kouchi M, Takahashi H (2008) J Am Chem Soc 130:2560CrossRef Gridnev ID, Imamoto T, Hoge G, Kouchi M, Takahashi H (2008) J Am Chem Soc 130:2560CrossRef
61.
go back to reference Enthaler S, Erre G, Junge K, Addis D, Kadyrov R, Beller M (2008) Chem Asian J 3:1104CrossRef Enthaler S, Erre G, Junge K, Addis D, Kadyrov R, Beller M (2008) Chem Asian J 3:1104CrossRef
62.
go back to reference Allwein SP, McWilliams JC, Secord EA, Mowrey DR, Nelson TD, Kress MH (2006) Tetrahedron Lett 47:6409CrossRef Allwein SP, McWilliams JC, Secord EA, Mowrey DR, Nelson TD, Kress MH (2006) Tetrahedron Lett 47:6409CrossRef
66.
go back to reference Hoen R, van den Berg M, Bernsmann H, Minnaard AJ, de Vries JG, Feringa BL (2004) Org Lett 6:1433CrossRef Hoen R, van den Berg M, Bernsmann H, Minnaard AJ, de Vries JG, Feringa BL (2004) Org Lett 6:1433CrossRef
67.
68.
70.
go back to reference Chen J, Zhang W, Geng H, Li W, Hou G, Lei A, Zhang X (2009) Angew Chem Int Ed 48:800CrossRef Chen J, Zhang W, Geng H, Li W, Hou G, Lei A, Zhang X (2009) Angew Chem Int Ed 48:800CrossRef
71.
72.
go back to reference 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 13:84CrossRef 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 13:84CrossRef
74.
75.
go back to reference Renaud JL, Dupau P, Hay AE, Guingouain M, Dixneuf PH, Bruneau C (2003) Adv Synth Catal 345:230CrossRef Renaud JL, Dupau P, Hay AE, Guingouain M, Dixneuf PH, Bruneau C (2003) Adv Synth Catal 345:230CrossRef
76.
go back to reference Jiang XB, Lefort L, Goudriaan PE, de Vires AHM, van Leeuwen PWNM, de Vries JG, Reek JNH (2006) Angew Chem Int Ed 45:1223CrossRef Jiang XB, Lefort L, Goudriaan PE, de Vires AHM, van Leeuwen PWNM, de Vries JG, Reek JNH (2006) Angew Chem Int Ed 45:1223CrossRef
79.
go back to reference Lennon IC, Ramsden JA, Brear CJ, Broady SD, Muir JC (2007) Tetrahedron Lett 48:4623CrossRef Lennon IC, Ramsden JA, Brear CJ, Broady SD, Muir JC (2007) Tetrahedron Lett 48:4623CrossRef
80.
82.
go back to reference 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 131:6683CrossRef 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 131:6683CrossRef
83.
go back to reference Stumpf A, Reynolds M, Sutherlin D, Babu S, Bappert E, Spindler F, Welch M, Gaudino J (2011) Adv Synth Catal 353:3367CrossRef Stumpf A, Reynolds M, Sutherlin D, Babu S, Bappert E, Spindler F, Welch M, Gaudino J (2011) Adv Synth Catal 353:3367CrossRef
84.
go back to reference Noyori R, Ohta M, Hsiao Y, Kitamura M, Ohta T, Takaya H (1986) J Am Chem Soc 108:7117CrossRef Noyori R, Ohta M, Hsiao Y, Kitamura M, Ohta T, Takaya H (1986) J Am Chem Soc 108:7117CrossRef
86.
go back to reference Cheruku P, Church TL, Trifonova A, Wartmann T, Andersson PG (2008) Tetrahedron Lett 49:7290CrossRef Cheruku P, Church TL, Trifonova A, Wartmann T, Andersson PG (2008) Tetrahedron Lett 49:7290CrossRef
89.
91.
Metadata
Title
Transition Metal-Catalyzed Enantioselective Hydrogenation of Enamides and Enamines
Authors
Qi-Lin Zhou
Jian-Hua Xie
Copyright Year
2014
Publisher
Springer Berlin Heidelberg
DOI
https://doi.org/10.1007/128_2013_482

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