Skip to main content
SpringerLink
Log in

Asymmetric Hydrogenation of Imines

  • Chapter
  • First Online:
Stereoselective Formation of Amines

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 343))

Abstract

Homogeneous catalytic asymmetric hydrogenation has evolved into a significantly useful methodology for the prepartion of enantiopure compounds. Significant advances in asymmetric hydrogenation of imines have enabled a straightforward and powerful approach to various chiral amines. An overview of the many variants of the chiral transition metal catalysts, illustrations of synthetic applications, and discussions of emerging and future strategies from a mechanistic perspective are presented.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Abbreviations

BARF:

(Tetrakis(3,5-bis(trifluoromethyl)phenyl)borate)

COD:

Cyclooctadiene

Cp:

Cyclopentadienyl

Cp*:

1,2,3,4,5-Pentamethylcyclopentadienyl

DCE:

Dichloroethane

D-DTTA:

Di-p-toluoyl-d-tartaric acid

DPEN:

1,2-Diphenylethane-1,2-diamine

MEA:

2-Methyl-5-ethylaniline

Py:

Pyridine

SPO:

Secondary phosphine oxide

TBME:

tert-Butyl methyl ether

TFE:

Trifluoroethanol

THF:

Tetrahydrofuran

TMI:

2,3,3-Trimethylindolenine

TOF:

Turnover frequency

TON:

Turnover number

Ts:

Tosyl (p-CH3C6H4SO2)

References

  1. Shang G, Li W, Zhang X (2010) In: Ojima I (ed) Catalytic asymmetric synthesis, 3rd edn. Wiley, New York, p 343

    Google Scholar 

  2. Chi Y, Tang W, Zhang X (2005) In: Evans PA (ed) Modern rhodium-catalyzed organic reactions. Wiley-VCH Verlag GmbH, Weinheim, p 1

    Google Scholar 

  3. Blaser H-U, Spindler F (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis. Springer, Berlin, p 247

    Google Scholar 

  4. Spindler F, Blaser H-U (2007) In: De Vries JG, Elsevier CJ (eds) Handbook of homogeneous hydrogenation. Wiley-VCH Verlag GmbH, Weinheim, p 1193

    Google Scholar 

  5. Ager D (2007) In: De Vries JG, Elsevier CJ (eds) Handbook of homogeneous hydrogenation. Wiley-VCH Verlag GmbH, Weinheim, p 745

    Google Scholar 

  6. Brown JM (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis. Springer, Berlin, p 121

    Google Scholar 

  7. Genet J-P (2008) In: Andersson PG, Munslow IJ (eds) Modern reduction methods. Wiley-VCH Verlag GmbH, Weinheim, p 3

    Google Scholar 

  8. Blaser H-U (2002) Adv Synth Catal 344:17

    CAS  Google Scholar 

  9. Noyori R (2002) Angew Chem. Int Ed 41:2008

    CAS  Google Scholar 

  10. Roseblade SJ, Pfaltz A (2007) Acc Chem Res 40:1402

    CAS  Google Scholar 

  11. Levi A, Modena G, Scorrano G (1975) J Chem Soc Chem Commun 6

    Google Scholar 

  12. Kang GJ, Cullen WR, Fryzuk MD, James BR, Kutney JP (1988) J Chem Soc. Chem Commun 1466

    Google Scholar 

  13. Bakos J, Orosz A, Heil B, Laghmari M, Lhoste P, Sinou D (1991) J Chem Soc. Chem Commun 1684

    Google Scholar 

  14. Buriak JM, Osborn JA (1996) Organometallics 15:3161

    CAS  Google Scholar 

  15. Tararov VI, Kadyrov R, Riermeier TH, Holz J, Borner A (1999) Tetrahedron Asymmetry 10:4009

    CAS  Google Scholar 

  16. Burk MJ, Feaster JE (1992) J Am Chem Soc 114:6266

    CAS  Google Scholar 

  17. Yoshikawa N, Tan L, McWilliams JC, Ramasamy D, Sheppard R (2010) Org Lett 12:276

    CAS  Google Scholar 

  18. Shang G, Yang Q, Zhang X (2006) Angew Chem. Int Ed 45:6360

    CAS  Google Scholar 

  19. Li C, Xiao J (2008) J Am Chem Soc 130:13208

    CAS  Google Scholar 

  20. Willoughby CA, Buchwald SL (1992) J Am Chem Soc 114:7562

    CAS  Google Scholar 

  21. Willoughby CA, Buchwald SL (1994) J Am Chem Soc 116:11703

    CAS  Google Scholar 

  22. Ringwald M, Stuermer R, Brintzinger HH (1999) J Am Chem Soc 121:1524

    CAS  Google Scholar 

  23. Oppolzer W, Wills M, Starkemann C, Bernardinelli G (1990) Tetrahedron Lett 31:4117

    CAS  Google Scholar 

  24. Charette AB, Giroux A (1996) Tetrahedron Lett 37:6669

    CAS  Google Scholar 

  25. Cobley CJ, Henschke JP (2003) Adv Synth Catal 345:195

    CAS  Google Scholar 

  26. Arai N, Utsumi N, Matsumoto Y, Murata K, Tsutsumi K, Ohkuma T (2012) Adv Synth Catal 354:2089

    CAS  Google Scholar 

  27. Shirai S-y, Nara H, Kayaki Y, Ikariya T (2009) Organometallics 28:802

    CAS  Google Scholar 

  28. Cheruku P, Church TL, Andersson PG (2008) Chem Asian J 3:1390

    CAS  Google Scholar 

  29. Chen F, Wang T, He Y, Ding Z, Li Z, Xu L, Fan Q-H (2011) Chem Eur J 17:1109

    CAS  Google Scholar 

  30. Chen F, Ding Z, Qin J, Wang T, He Y, Fan Q-H (2011) Org Lett 13:4348

    CAS  Google Scholar 

  31. Crabtree RH, Felkin H, Morris GE (1976) J Chem Soc. Chem Commun 716

    Google Scholar 

  32. Spindler F, Pugin B, Blaser H-U (1990) Angew Chem. Int Ed Engl 29:558

    Google Scholar 

  33. Blaser H-U, Schmidt E (2004) Asymmetric catalysis on industrial scale: challenges, approaches and solutions. Wiley-VCH Verlag GmbH, Weinheim

    Google Scholar 

  34. Blaser H-U, Buser H-P, Coers K, Hanreich R, Jalett H-P, Jelsch E, Pugin B, Schneider H-D, Spindler F, Wegmann A (1999) Chimia 53:275

    CAS  Google Scholar 

  35. Morimoto T, Nakajima N, Achiwa K (1994) Chem Pharm Bull 42:1951

    CAS  Google Scholar 

  36. Liu D, Li W, Zhang X (2004) Tetrahedron Asymmetry 15:2181

    CAS  Google Scholar 

  37. Morimoto T, Nakajima N, Achiwa K (1995) Synlett 748

    Google Scholar 

  38. Zhu G, Zhang X (1998) Tetrahedron Asymmetry 9:2415

    CAS  Google Scholar 

  39. Morimoto T, Suzuki N, Achiwa K (1998) Tetrahedron Asymmetry 9:183

    CAS  Google Scholar 

  40. Blaser HU, Buser HP, Hausel R, Jalett HP, Spindler F (2001) J Organomet Chem 621:34

    CAS  Google Scholar 

  41. Reetz MT, Beuttenmuller EW, Goddard R, Pasto M (1999) Tetrahedron Lett 40:4977

    CAS  Google Scholar 

  42. Xiao D, Zhang X (2001) Angew Chem. Int Ed 40:3425

    CAS  Google Scholar 

  43. Hou G, Gosselin F, Li W, McWilliams JC, Sun Y, Weisel M, O’Shea PD, Chen C-y, Davies IW, Zhang X (2009) J Am Chem Soc 131:9882

    CAS  Google Scholar 

  44. Hou G, Li W, Ma M, Zhang X, Zhang X (2010) J Am Chem Soc 132:12844

    CAS  Google Scholar 

  45. Wang Y-Q, Yu C-B, Wang D-W, Wang X-B, Zhou Y-G (2008) Org Lett 10:2071

    CAS  Google Scholar 

  46. Yu C-B, Wang D-W, Zhou Y-G (2009) J Org Chem 74:5633

    CAS  Google Scholar 

  47. Chang M, Li W, Hou G, Zhang X (2010) Adv Synth Catal 352:3121

    CAS  Google Scholar 

  48. Chang M, Li W, Zhang X (2011) Angew Chem. Int Ed 50:10679

    CAS  Google Scholar 

  49. Dervisi A, Carcedo C, Ooi L-I (2006) Adv Synth Catal 348:175

    CAS  Google Scholar 

  50. Smidt SP, Pfaltz A, Martinez-Viviente E, Pregosin PS, Albinati A (2003) Organometallics 22:1000

    CAS  Google Scholar 

  51. Imamoto T, Iwadate N, Yoshida K (2006) Org Lett 8:2289

    CAS  Google Scholar 

  52. Li W, Hou G, Chang M, Zhang X (2009) Adv Synth Catal 351:3123

    CAS  Google Scholar 

  53. Lightfoot A, Schnider P, Pfaltz A (1998) Angew Chem. Int Ed 37:2897

    CAS  Google Scholar 

  54. Kaiser S, Smidt SP, Pfaltz A (2006) Angew Chem Int Ed 45:5194

    Google Scholar 

  55. Hedberg C, Källström K, Brandt P, Hansen LK, Andersson PG (2006) J Am Chem Soc 128:2995

    CAS  Google Scholar 

  56. Liu Q-B, Yu C-B, Zhou Y-G (2006) Tetrahedron Lett 47:4733

    CAS  Google Scholar 

  57. Barchuk A, Ngai M-Y, Krische MJ (2007) J Am Chem Soc 129:8432

    CAS  Google Scholar 

  58. Schönleber M, Hilgraf R, Pfaltz A (2008) Adv Synth Catal 350:2033

    Google Scholar 

  59. Wang A, Wüstenberg B, Pfaltz A (2008) Angew Chem Int Ed 47:2298

    CAS  Google Scholar 

  60. Church TL, Andersson PG (2008) Coord Chem Rev 252:513

    CAS  Google Scholar 

  61. Dorta R, Broggini D, Stoop R, Rüegger H, Spindler F, Togni A (2004) Chem Eur J 10:267

    CAS  Google Scholar 

  62. Yamagata T, Tadaoka H, Nagata M, Hirao T, Kataoka Y, Ratovelomanana-Vidal V, Genet JP, Mashima K (2006) Organometallics 25:2505

    CAS  Google Scholar 

  63. Schnider P, Koch G, Pretot R, Wang G, Bohnen FM, Kruger C, Pfaltz A (1997) Chem Eur J 3:887

    CAS  Google Scholar 

  64. Kainz S, Brinkmann A, Leitner W, Pfaltz A (1999) J Am Chem Soc 121:6421

    CAS  Google Scholar 

  65. Menges F, Pfaltz A (2002) Adv Synth Catal 344:40

    CAS  Google Scholar 

  66. Smidt SP, Menges F, Pfaltz A (2004) Org Lett 6:2023

    CAS  Google Scholar 

  67. Schrems MG, Pfaltz A (2009) Chem Commun 6210

    Google Scholar 

  68. Baeza A, Pfaltz A (2010) Chem Eur J 16:4003

    CAS  Google Scholar 

  69. Cozzi PG, Menges F, Kaiser S (2003) Synlett 833

    Google Scholar 

  70. Lu W-J, Chen Y-W, Hou X-L (2010) Adv Synth Catal 352:103

    CAS  Google Scholar 

  71. Zhu S-F, Xie J-B, Zhang Y-Z, Li S, Zhou Q-L (2006) J Am Chem Soc 128:12886

    CAS  Google Scholar 

  72. Han Z, Wang Z, Zhang X, Ding K (2009) Angew Chem. Int Ed 48:5345

    CAS  Google Scholar 

  73. Moessner C, Bolm C (2005) Angew Chem. Int Ed 44:7564

    CAS  Google Scholar 

  74. Cheemala MN, Knochel P (2007) Org Lett 9:3089

    CAS  Google Scholar 

  75. Guiu E, Munoz B, Castillon S, Claver C (2003) Adv Synth Catal 345:169

    CAS  Google Scholar 

  76. Guiu E, Aghmiz M, Diaz Y, Claver C, Meseguer B, Militzer C, Castillon S (2006) Eur J Org Chem 627

    Google Scholar 

  77. Vargas S, Rubio M, Suarez A, Pizzano A (2005) Tetrahedron Lett 46:2049

    CAS  Google Scholar 

  78. van den Berg M, Haak RM, Minnaard AJ, de Vries AHM, de Vries JG, Feringa BL (2002) Adv Synth Catal 344:1003

    Google Scholar 

  79. van den Berg M, Minnaard AJ, Haak RM, Leeman M, Schudde EP, Meetsma A, Feringa BL, de Vries AHM, Maljaars CEP, Willans CE, Hyett D, Boogers JAF, Henderickx HJW, de Vries JG (2003) Adv Synth Catal 345:308

    Google Scholar 

  80. Faller JW, Milheiro SC, Parr J (2006) J Organomet Chem 691:4945

    CAS  Google Scholar 

  81. Mrsic N, Minnaard AJ, Feringa BL, de Vries JG (2009) J Am Chem Soc 131:8358

    CAS  Google Scholar 

  82. Mrsic N, Lefort L, Boogers JAF, Minnaard AJ, Feringa BL, de Vries JG (2008) Adv Synth Catal 350:1081

    CAS  Google Scholar 

  83. Mrsic N, Jerphagnon T, Minnaard AJ, Feringa BL, de Vries JG (2010) Tetrahedron Asymmetry 21:7

    CAS  Google Scholar 

  84. Xie J-H, Yan P-C, Zhang Q-Q, Yuan K-X, Zhou Q-L (2012) ACS Catal 2:561

    CAS  Google Scholar 

  85. Hou C-J, Wang Y-H, Zheng Z, Xu J, Hu X-P (2012) Org Lett 14:3554

    CAS  Google Scholar 

  86. Reetz MT, Bondarev O (2007) Angew Chem. Int Ed 46:4523

    CAS  Google Scholar 

  87. Li C, Wang C, Villa-Marcos B, Xiao J (2008) J Am Chem Soc 130:14450

    CAS  Google Scholar 

  88. Morimoto T, Achiwa K (1995) Tetrahedron Asymmetry 6:2661

    CAS  Google Scholar 

  89. Hou G-H, Xie J-H, Yan P-C, Zhou Q-L (2009) J Am Chem Soc 131:1366

    CAS  Google Scholar 

  90. Yan P-C, Xie J-H, Hou G-H, Wang L-X, Zhou Q-L (2009) Adv Synth Catal 351:3243

    CAS  Google Scholar 

  91. Wang W-B, Lu S-M, Yang P-Y, Han X-W, Zhou Y-G (2003) J Am Chem Soc 125:10536

    CAS  Google Scholar 

  92. Wang X-B, Zhou Y-G (2008) J Org Chem 73:5640

    CAS  Google Scholar 

  93. Wang D-W, Wang X-B, Wang D-S, Lu S-M, Zhou Y-G, Li Y-X (2009) J Org Chem 74:2780

    CAS  Google Scholar 

  94. Tang W-J, Zhu S-F, Xu L-J, Zhou Q-L, Fan Q-H, Zhou H-F, Lam K, Chan ASC (2007) Chem Commun 613

    Google Scholar 

  95. Gou F-R, Li W, Zhang X, Liang Y-M (2010) Adv Synth Catal 352:2441

    CAS  Google Scholar 

  96. Tang W, Xu L, Fan Q-H, Wang J, Fan B, Zhou Z, K-h L, Chan ASC (2009) Angew Chem. Int Ed 48:9135

    CAS  Google Scholar 

  97. Legault CY, Charette AB (2005) J Am Chem Soc 127:8966

    CAS  Google Scholar 

  98. Wang X-B, Zeng W, Zhou Y-G (2008) Tetrahedron Lett 49:4922

    CAS  Google Scholar 

  99. Tang W-J, Tan J, Xu L-J, Lam K-H, Fan Q-H, Chan ASC (2010) Adv Synth Catal 352:1055

    CAS  Google Scholar 

  100. Tang W, Sun Y, Xu L, Wang T, Fan Q, Lam K-H, Chan ASC (2010) Org Biomol Chem 8:3464

    CAS  Google Scholar 

  101. Satoh K, Inenaga M, Kanai K (1998) Tetrahedron Asymmetry 9:2657

    CAS  Google Scholar 

  102. Chan YNC, Meyer D, Osborn JA (1990) J Chem Soc. Chem Commun 869

    Google Scholar 

  103. Ng Cheong Chan Y, Osborn JA (1990) J Am Chem Soc 112:9400

    CAS  Google Scholar 

  104. Blaser H-U, Pugin B, Spindler F, Togni A (2002) C R Chimie 5:379

    CAS  Google Scholar 

  105. Jiang X-B, Minnaard AJ, Hessen B, Feringa BL, Duchateau ALL, Andrien JGO, Boogers JAF, de VJG (2003) Org Lett 5:1503

    CAS  Google Scholar 

  106. Tani K, Onouchi J-i, Yamagata T, Kataoka Y (1995) Chem Lett 955

    Google Scholar 

  107. Morimoto T, Suzuki N, Achiwa K (1996) Heterocycles 43:2557

    CAS  Google Scholar 

  108. Tietze LF, Ila H, Bell HP (2004) Chem Rev 104:3453

    CAS  Google Scholar 

  109. Chen Q-A, Ye Z-S, Duan Y, Zhou Y-G (2013) Chem Soc Rev 42:497

    CAS  Google Scholar 

  110. Abe H, Amii H, Uneyama K (2001) Org Lett 3:313

    CAS  Google Scholar 

  111. Shuklov IA, Dubrovina NV, Börner A (2007) Synthesis 2007:2925

    Google Scholar 

  112. Yang Q, Shang G, Gao W, Deng J, Zhang X (2006) Angew Chem. Int Ed 45:3832

    CAS  Google Scholar 

  113. Wang Y-Q, Zhou Y-G (2006) Synlett 1189

    Google Scholar 

  114. Wang Y-Q, Lu S-M, Zhou Y-G (2007) J Org Chem 72:3729

    CAS  Google Scholar 

  115. Wang D-S, Chen Q-A, Li W, Yu C-B, Zhou Y-G, Zhang X (2010) J Am Chem Soc 132:8909

    CAS  Google Scholar 

  116. Marcazzan P, Patrick BO, James BR (2003) Organometallics 22:1177

    CAS  Google Scholar 

  117. Yu Z, Jin W, Jiang Q (2012) Angew Chem. Int Ed 51:6060

    CAS  Google Scholar 

  118. Magee MP, Norton JR (2001) J Am Chem Soc 123:1778

    CAS  Google Scholar 

  119. Hou G, Tao R, Sun Y, Zhang X, Gosselin F (2010) J Am Chem Soc 132:2124

    CAS  Google Scholar 

  120. Zhou X-Y, Bao M, Zhou Y-G (2011) Adv Synth Catal 353:84

    CAS  Google Scholar 

  121. Gao K, Yu C-B, Li W, Zhou Y-G, Zhang X (2011) Chem Commun 47:7845

    CAS  Google Scholar 

  122. Wang D-S, Tang J, Zhou Y-G, Chen M-W, Yu C-B, Duan Y, Jiang G-F (2011) Chem Sci 2:803

    CAS  Google Scholar 

  123. Wang D-S, Ye Z-S, Chen Q-A, Zhou Y-G, Yu C-B, Fan H-J, Duan Y (2011) J Am Chem Soc 133:8866

    CAS  Google Scholar 

  124. Burk MJ, Martinez JP, Feaster JE, Cosford N (1994) Tetrahedron 50:4399

    CAS  Google Scholar 

  125. Spindler F, Blaser H-U (2001) Adv Synth Catal 343:68

    CAS  Google Scholar 

  126. Chi Y, Zhou Y-G, Zhang X (2003) J Org Chem 68:4120

    CAS  Google Scholar 

  127. Hoffmann S, Nicoletti M, List B (2006) J Am Chem Soc 128:13074

    CAS  Google Scholar 

  128. Storer RI, Carrera DE, Ni Y, MacMillan DWC (2005) J Am Chem Soc 128:84

    Google Scholar 

  129. Tang W, Zhang X (2003) Chem Rev 103:3029

    CAS  Google Scholar 

  130. Xie J-H, Zhu S-F, Zhou Q-L (2011) Chem Rev 111:1713

    CAS  Google Scholar 

  131. Trifonova A, Diesen JS, Chapman CJ, Andersson PG (2004) Org Lett 6:3825

    CAS  Google Scholar 

  132. Abdur-Rashid K, Lough AJ, Morris RH (2001) Organometallics 20:1047

    CAS  Google Scholar 

  133. Blanc C, Agbossou-Niedercorn F, Nowogrocki G (2004) Tetrahedron Asymmetry 15:2159

    CAS  Google Scholar 

  134. Cobley CJ, Foucher E, Lecouve J-P, Lennon IC, Ramsden JA, Thominot G (2003) Tetrahedron Asymmetry 14:3431

    CAS  Google Scholar 

  135. Wild FRWP, Zsolnai L, Huttner G, Brintzinger HH (1982) J Organomet Chem 232:233

    CAS  Google Scholar 

  136. Willoughby CA, Buchwald SL (1994) J Am Chem Soc 116:8952

    CAS  Google Scholar 

  137. Gao K, Wu B, Yu C-B, Chen Q-A, Ye Z-S, Zhou Y-G (2012) Org Lett 14:3890

    CAS  Google Scholar 

  138. Gao K, Yu C-B, Wang D-S, Zhou Y-G (2012) Adv Synth Catal 354:483

    CAS  Google Scholar 

  139. Jackson M, Lennon IC (2007) Tetrahedron Lett 48:1831

    CAS  Google Scholar 

  140. Berhal F, Wu Z, Zhang Z, Ayad T, Ratovelomanana-Vidal V (2012) Org Lett 14:3308

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemical Biology and Drug Discovery, Stony Brook University, Stony Brook, NY, 11794-3400, USA

    Wei Li

  2. Departments of Chemistry and Chemical Biology, Department of Medicinal Chemistry, Rutgers, the State University of New Jersey, 160 Frelinghuysen Rd, Piscataway, NJ, 08854, USA

    Xumu Zhang

Authors
  1. Wei Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xumu Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Xumu Zhang .

Editor information

Editors and Affiliations

  1. Institute of Chemical Biology and Drug Discovery, Stony Brook University, Stony Brook, New York, USA

    Wei Li

  2. Department of Chemistry & Chemical Biology, Department of Medicinal Chemistry, Rutgers, The State University of New Jersey, Piscataway, New Jersey, USA

    Xumu Zhang

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Li, W., Zhang, X. (2013). Asymmetric Hydrogenation of Imines. 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_483

Download citation

Publish with us

Policies and ethics

Search

Navigation