Skip to main content
SpringerLink
Log in

Asymmetric Reductive Amination

  • Chapter
  • First Online:
Book cover Stereoselective Formation of Amines

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

Abstract

Asymmetric reductive amination (ARA) affords synthetically valuable chiral amines straightforwardly. This chapter reviews the recent advances made in the area, focusing on ARA by hydrogenation, transfer hydrogenation, organocatalytic reduction, and biocatalytic reduction.

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

References

  1. Kobayashi S, Ishitani H (1999) Chem Rev 99:1069–1094

    Article  CAS  Google Scholar 

  2. Ellman JA, Owens TD, Tang TP (2002) Acc Chem Res 35:984–995

    Article  CAS  Google Scholar 

  3. Gomez S, Peters JA, Maschmeyer T (2002) Adv Synth Catal 344:1037–1057

    Article  CAS  Google Scholar 

  4. Besson M, Pinel C (2003) Top Catal 25:43–61

    Article  CAS  Google Scholar 

  5. Blaser H-U, Malan C, Pugin B, Spindler F, Steiner H, Studer M (2003) Adv Synth Catal 345:103–151

    Article  CAS  Google Scholar 

  6. Ellman JA (2003) Pure Appl Chem 75:39–46

    Article  CAS  Google Scholar 

  7. Kukula P, Prins R (2003) Top Catal 25:29–42

    Article  CAS  Google Scholar 

  8. Breuer M, Ditrich K, Habicher T, Hauer B, Keßeler M, Stürmer R, Zelinski T (2004) Angew Chem Int Ed 43:788–824

    Article  CAS  Google Scholar 

  9. Friestad GK (2005) Eur J Org Chem 2005:3157–3172

    Article  Google Scholar 

  10. Tararov VI, Börner A (2005) Synlett 2005:203–211

    Article  Google Scholar 

  11. Abdel-Magid AF, Mehrman SJ (2006) Org Proc Res Dev 10:971–1031

    Article  CAS  Google Scholar 

  12. Morton D, Stockman RA (2006) Tetrahedron 62:8869–8905

    Article  CAS  Google Scholar 

  13. Ramachandran PV, Burghardt TE (2006) Pure Appl Chem 78:1397–1406

    Article  CAS  Google Scholar 

  14. Friestad GK, Mathies AK (2007) Tetrahedron 63:2541–2569

    Article  CAS  Google Scholar 

  15. Kizirian J-C (2007) Chem Rev 108:140–205

    Article  Google Scholar 

  16. Minnaard AJ, Feringa BL, Lefort L, de Vries JG (2007) Acc Chem Res 40:1267–1277

    Article  CAS  Google Scholar 

  17. Petrini M, Torregiani E (2007) Synthesis 2007:159–186

    Article  Google Scholar 

  18. Skucas E, Ngai M-Y, Komanduri V, Krische MJ (2007) Acc Chem Res 40:1394–1401

    Article  CAS  Google Scholar 

  19. You SL (2007) Chem Asian J 2:820–827

    Article  CAS  Google Scholar 

  20. Spindler F, Blaser HU (2008) Enatioselective hydrogenation of C=N functions and enamines. In: The handbook of homogeneous hydrogenation. Wiley-VCH GmbH, p 1193

    Google Scholar 

  21. Muller TE, Hultzsch KC, Yus M, Foubelo F, Tada M (2008) Chem Rev 108:3795–3892

    Article  Google Scholar 

  22. Tripathi RP, Verma SS, Pandey J, Tiwari VK (2008) Curr Org Chem 12:1093–1115

    Article  CAS  Google Scholar 

  23. Nugent TC, El-Shazly M (2010) Adv Synth Catal 352:753–819

    Article  CAS  Google Scholar 

  24. Wang C, Villa-Marcos B, Xiao JL (2011) Chem Commun 47:9773–9785

    Article  CAS  Google Scholar 

  25. Abdel-Magid AF, Carson KG, Harris BD, Maryanoff CA, Shah RD (1996) J Org Chem 61:3849–3862

    Article  CAS  Google Scholar 

  26. Burkhardt ER, Matos K (2006) Chem Rev 106:2617–2650

    Article  CAS  Google Scholar 

  27. Gribble GW (2006) Org Proc Res Dev 10:1062–1075

    Article  CAS  Google Scholar 

  28. Noyori R, Ohkuma T (2001) Angew Chem Int Ed 40:40–73

    Article  CAS  Google Scholar 

  29. Blaser HU, Buser HP, Jalett HP, Pugin B, Spindler F (1999) Synlett 867–868

    Google Scholar 

  30. Xiao D, Zhang XM (2001) Angew Chem Int Ed 40:3425–3428

    Article  CAS  Google Scholar 

  31. Chi YX, Zhou YG, Zhang XM (2003) J Org Chem 68:4120–4122

    Article  CAS  Google Scholar 

  32. Tararov VI, Kadyrov R, Riermeier TH, Borner A (2000) Chem Commun 1867–1868

    Google Scholar 

  33. Kadyrov R, Riermeier TH, Dingerdissen U, Tararov V, Borner A (2003) J Org Chem 68:4067–4070

    Article  CAS  Google Scholar 

  34. Hsiao Y, Rivera NR, Rosner T, Krska SW, Njolito E, Wang F, Sun Y, Armstrong JD, Grabowski EJJ, Tillyer RD, Spindler F, Malan C (2004) J Am Chem Soc 126:9918–9919

    Article  CAS  Google Scholar 

  35. Bunlaksananusorn T, Rampf F (2005) Synlett 17:2682–2684

    Article  Google Scholar 

  36. Steinhuebel D, Sun Y, Matsumura K, Sayo N, Saito T (2009) J Am Chem Soc 131:11316–11317

    Article  CAS  Google Scholar 

  37. Li CQ, Wang C, Villa-Marcos B, Xiao JL (2008) J Am Chem Soc 130:14450–14451

    Article  CAS  Google Scholar 

  38. Tang WJ, Johnston S, Iggo JA, Berry NG, Phelan M, Lian L, Bacsa J, Xiao JL (2013) Angew Chem Int Ed 52:1668–1672

    Article  CAS  Google Scholar 

  39. Li C, Villa-Marcos B, Xiao JL (2009) J Am Chem Soc 131:6967–6969

    Article  CAS  Google Scholar 

  40. Rubio-Pérez L, Pérez-Flores FJ, Sharma P, Velasco L, Cabrera A (2009) Org Lett 11:265–268

    Article  Google Scholar 

  41. Zassinovich G, Mestroni G, Gladiali S (1992) Chem Rev 92:1051–1069

    Article  CAS  Google Scholar 

  42. de Graauw CF, Peters JA, van Bekkum H, Huskens J (1994) Synthesis 1994:1007–1017

    Article  Google Scholar 

  43. Noyori R, Hashiguchi S (1997) Acc Chem Res 30:97–102

    Article  CAS  Google Scholar 

  44. Palmer MJ, Wills M (1999) Tetrahedron Asymmetry 10:2045–2061

    Article  CAS  Google Scholar 

  45. Wills M, Palmer M, Smith A, Kenny J, Walsgrove T (2000) Molecules 5:4–18

    Article  CAS  Google Scholar 

  46. Everaere K, Mortreux A, Carpentier JF (2003) Adv Synth Catal 345:67–77

    Article  CAS  Google Scholar 

  47. Clapham SE, Hadzovic A, Morris RH (2004) Coord Chem Rev 248:2201–2237

    Article  CAS  Google Scholar 

  48. Gladiali S, Alberico E (2006) Chem Soc Rev 35:226–236

    Article  CAS  Google Scholar 

  49. Samec JSM, Backvall JE, Andersson PG, Brandt P (2006) Chem Soc Rev 35:237–248

    Article  CAS  Google Scholar 

  50. Ikariya T, Blacker AJ (2007) Acc Chem Res 40:1300–1308

    Article  CAS  Google Scholar 

  51. Wu XF, Xiao JL (2007) Chem Commun 2449–2466

    Google Scholar 

  52. Wang C, Wu XF, Xiao JL (2008) Chem Asian J 3:1750–1770

    Article  CAS  Google Scholar 

  53. Wu XF, Wang C, Xiao JL (2010) Platinum Met Rev 54:3–19

    Article  CAS  Google Scholar 

  54. Kadyrov R, Riermeier TH (2003) Angew Chem Int Ed 42:5472–5474

    Article  CAS  Google Scholar 

  55. Williams GD, Pike RA, Wade CE, Wills M (2003) Org Lett 5:4227–4230

    Article  CAS  Google Scholar 

  56. Uematsu N, Fujii A, Hashiguchi S, Ikariya T, Noyori R (1996) J Am Chem Soc 118:4916–4917

    Article  CAS  Google Scholar 

  57. Strotman NA, Baxter CA, Brands KMJ, Cleator E, Krska SW, Reamer RA, Wallace DJ, Wright TJ (2011) J Am Chem Soc 133:8362–8371

    Article  CAS  Google Scholar 

  58. Ouellet SG, Walji AM, Macmillan DWC (2007) Acc Chem Res 40:1327–1339

    Article  CAS  Google Scholar 

  59. Iwasaki F, Onomura O, Mishima K, Kanematsu T, Maki T, Matsumura Y (2001) Tetrahedron Lett 42:2525–2527

    Article  CAS  Google Scholar 

  60. Malkov AV, Mariani A, MacDougall KN, Kocovský P (2004) Org Lett 6:2253–2256

    Article  CAS  Google Scholar 

  61. Malkov AV, Stončius S, MacDougall KN, Mariani A, McGeoch GD, Kočovský P (2006) Tetrahedron 62:264–284

    Article  CAS  Google Scholar 

  62. Malkov AV, Vranková K, Stončius S, Kočovský P (2009) J Org Chem 74:5839–5849

    Article  CAS  Google Scholar 

  63. Wang ZY, Ye XX, Wei SY, Wu PC, Zhang AJ, Sun J (2006) Org Lett 8:999–1001

    Article  CAS  Google Scholar 

  64. Gautier F-M, Jones S, Martin SJ (2009) Org Biomol Chem 7:229–231

    Article  CAS  Google Scholar 

  65. Malkov AV, Stončius S, Kočovský P (2007) Angew Chem Int Ed 46:3722–3724

    Article  CAS  Google Scholar 

  66. Guizzetti S, Benaglia M, Cozzi F, Annunziata R (2009) Tetrahedron 65:6354–6363

    Article  CAS  Google Scholar 

  67. Gautier F-M, Jones S, Li X, Martin SJ (2011) Org Biomol Chem 9:7860–7868

    Article  CAS  Google Scholar 

  68. Singh S, Batra UK (1989) Indian J Chem B 28:1

    Google Scholar 

  69. Rueping M, Sugiono E, Azap C, Theissmann T, Bolte M (2005) Org Lett 7:3781–3783

    Article  CAS  Google Scholar 

  70. Hoffmann S, Seayad AM, List B (2005) Angew Chem Int Ed 44:7424–7427

    Article  CAS  Google Scholar 

  71. Storer RI, Carrera DE, Ni Y, MacMillan DWC (2006) J Am Chem Soc 128:84–86

    Article  CAS  Google Scholar 

  72. Akiyama T, Itoh J, Yokota K, Fuchibe K (2004) Angew Chem Int Ed 43:1566–1568

    Article  CAS  Google Scholar 

  73. Uraguchi D, Terada M (2004) J Am Chem Soc 126:5356–5357

    Article  CAS  Google Scholar 

  74. Li G, Liang Y, Antilla JC (2007) J Am Chem Soc 129:5830–5831

    Article  CAS  Google Scholar 

  75. Wakchaure VN, Nicoletti M, Ratjen L, List B (2010) Synlett 2010:2708–2710

    Article  Google Scholar 

  76. Hoffmann S, Nicoletti M, List B (2006) J Am Chem Soc 128:13074–13075

    Article  CAS  Google Scholar 

  77. Zhou J, List B (2007) J Am Chem Soc 129:7498–7499

    Article  CAS  Google Scholar 

  78. Kumar A, Sharma S, Maurya RA (2010) Adv Synth Catal 352:2227–2232

    Article  CAS  Google Scholar 

  79. Zhu C, Akiyama T (2010) Adv Synth Catal 352:1846–1850

    Article  CAS  Google Scholar 

  80. Hummel W, Kula M-R (1989) Eur J Biochem 184:1–13

    Article  CAS  Google Scholar 

  81. Bommarius AS, Schwarm M, Stingl K, Kottenhahn M, Huthmacher K, Drauz K (1995) Tetrahedron Asymmetry 6:2851–2888

    Article  CAS  Google Scholar 

  82. Hall M, Bommarius AS (2011) Chem Rev 111:4088–4110

    Article  CAS  Google Scholar 

  83. Hollmann F, Arends IWCE, Holtmann D (2011) Green Chem 13:2285–2314

    Article  CAS  Google Scholar 

  84. Ricca E, Brucher B, Schrittwieser JH (2011) Adv Synth Catal 353:2239–2262

    Article  CAS  Google Scholar 

  85. Patel RN (2011) ACS Catal 1:1056–1074

    Article  CAS  Google Scholar 

  86. Wildeman SMAD, Sonke T, Schoemaker HE, May O (2007) Acc Chem Res 40:1260–1266

    Article  Google Scholar 

  87. Sanwal BD, Zink MW (1961) Arch Biochem Biophys 94:430–435

    Article  CAS  Google Scholar 

  88. Bommarius AS, Drauz K, Gunther K, Knaup G, Schwarm M (1997) Tetrahedron Asymmetry 8:3197–3200

    Article  CAS  Google Scholar 

  89. Krix G, Bommarius AS, Drauz K, Kottenhahn M, Schwarm M, Kula MR (1997) J Biotechnol 53:29–39

    Article  CAS  Google Scholar 

  90. Hanson RL, Schwinden MD, Banerjee A, Brzozowski DB, Chen B-C, Patel BP, McNamee CG, Kodersha GA, Kronenthal DR, Patel RN, Szarka LJ (1999) Bioorg Med Chem 7:2247–2252

    Article  CAS  Google Scholar 

  91. Gröger H, May O, Werner H, Menzel A, Altenbuchner J (2006) Org Proc Res Dev 10:666–669

    Article  Google Scholar 

  92. Hanson RL, Howell JM, LaPorte TL, Donovan MJ, Cazzulino DL, Zannella V, Montana MA, Nanduri VB, Schwarz SR, Eiring RF, Durand SC, Wasylyk JM, Parker WL, Liu MS, Okuniewicz FJ, Chen B-C, Harris JC, Natalie KJ Jr, Ramig K, Swaminathan S, Rosso VW, Pack SK, Lotz BT, Bernot PJ, Rusowicz A, Lust DA, Tse KS, Venit JJ, Szarka LJ, Patel RN (2000) Enzyme Microb Technol 26:348–358

    Article  CAS  Google Scholar 

  93. Cainelli G, Engel PC, Galletti P, Giacomini D, Gualandi A, Paradisi F (2005) Org Biomol Chem 3:4316–4320

    Article  CAS  Google Scholar 

  94. Vedha-Peters K, Gunawardana M, Rozzell JD, Novick SJ (2006) J Am Chem Soc 128:10923–10929

    Article  CAS  Google Scholar 

  95. Galkin A, Kulakova L, Yoshimura T, Soda K, Esaki N (1997) Appl Environ Microbiol 63:4651–4656

    CAS  Google Scholar 

  96. Menzel A, Werner H, Altenbuchner J, Gröger H (2004) Eng Life Sci 4:573–576

    Article  CAS  Google Scholar 

  97. Höhne M, Kühl S, Robins K, Bornscheuer UT (2008) Chembiochem 9:363–365

    Article  Google Scholar 

  98. Fuchs M, Koszelewski D, Tauber K, Kroutil W, Faber K (2010) Chem Commun 46:5500–5502

    Article  CAS  Google Scholar 

  99. Cassimjee KE, Branneby C, Abedi V, Wells A, Berglund P (2010) Chem Commun 46:5569–5571

    Article  CAS  Google Scholar 

  100. Truppo MD, Rozzell JD, Turner NJ (2009) Org Proc Res Dev 14:234–237

    Article  Google Scholar 

  101. Koszelewski D, Lavandera I, Clay D, Guebitz GM, Rozzell D, Kroutil W (2008) Angew Chem Int Ed 47:9337–9340

    Article  CAS  Google Scholar 

  102. Desai AA (2011) Angew Chem Int Ed 50:1974–1976

    Article  CAS  Google Scholar 

  103. Savile CK, Janey JM, Mundorff EC, Moore JC, Tam S, Jarvis WR, Colbeck JC, Krebber A, Fleitz FJ, Brands J, Devine PN, Huisman GW, Hughes GJ (2010) Science 329:305–309

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Key Laboratory of Applied Surface and Colloid Chemistry of Ministry of Education, and Department of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, China

    Chao Wang & Jianliang Xiao

  2. Department of Chemistry, University of Liverpool, Liverpool, L69 7ZD, UK

    Jianliang Xiao

Authors
  1. Chao Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jianliang Xiao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Chao Wang or Jianliang Xiao .

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

Wang, C., Xiao, J. (2013). Asymmetric Reductive Amination. 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_484

Download citation

Publish with us

Policies and ethics

Search

Navigation