Reversal of enantioselectivity by catalyst protonation: Asymmetric hydrocyanation of imines with oxazaborolidines

Synlett

Volumn , Issue 1, 2006, Pages 41-44

  Berkessel, Albrecht ^a   Mukherjee, Santanu ^a   Lex, Johann ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Asymmetric catalysis; Hydrocyanation; Imine; Oxazaborolidine; Protonation

Indexed keywords

HYDROGEN CYANIDE; IMINE; OXAZABOROLIDINE DERIVATIVE;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON TRANSPORT; X RAY CRYSTALLOGRAPHY;

EID: 30544445787     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-922757     Document Type: Article

References (34)

1. Corey, E. J.; Helal, C. J. Angew. Chem. Int. Ed. 1998, 37, 1986.
2. Hirao, A.; Itsuno, S.; Nakahama, S.; Yamazaki, N. J. Chem. Soc., Chem. Commun. 1981, 314.
3. (a) Corey, E. J.; Shibata, T.; Lee, T. W. J. Am. Chem. Soc. 2002, 124, 3808.
4. (b) Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc. 2002, 124, 9992.
5. (c) Zhou, G.; Hu, Q.-Y.; Corey, E. J. Org. Lett. 2003, 5, 3979.
6. (d) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 6388.
7. (e) Ryu, D. H.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 4800.
8. (f) Hu, Q.-Y.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 13708.
9. (g) Ryu, D. H.; Zhou, G.; Corey, E. J. Org. Lett. 2005, 7, 1633.
10. (h) Corey, E. J. Angew. Chem. Int. Ed. 2002, 41, 1650.
11. (a) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8106.
12. (b) Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384.
13. For previous reports on asymmetric hydrocyanation of imines, see: (a) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 4901.
14. (b) Sigman, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 5315.
15. (c) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157.
16. (d) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirachun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284.
17. (e) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
18. (f) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2000, 39, 1279.
19. (g) Takamura, M.; Hamashima, Y.; Usuda, H.; Kanai, M.; Shibasaki, M. Angew. Chem. Int. Ed. 2000, 39, 1650.
20. (h) Josephsohn, N. S.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 11594.
21. (i) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
22. (j) Wenzel, A. G.; Lalonde, M. P.; Jacobsen, E. N. Synlett 2003, 1919.
23. (k) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634.
24. Huang, J.; Corey, E. J. Org. Lett. 2004, 6, 5027.
25. For an excellent review about asymmetric hydocyanation of imines see: (a) Gröger, H. Chem. Rev. 2003, 103, 2795
26. . See also: (b) Yet, L. Angew. Chem. Int. Ed. 2001, 40, 875.
27. (c) Spino, C. Angew. Chem. Int. Ed. 2004, 43, 1764.
28. (d) Berkessel, A.; Gröger, H. Asymmetric Organocatalysis; Wiley-VCH: Weinheim, 2005.
29. The absolute configurations of the product α-amino nitriles 4 were determined by comparing the sense of optical rotation with literature data: (a) Hassan, N. A.; Bayer, E.; Jochims, J. C. J. Chem. Soc., Perkin Trans. 1 1998, 3747.
30. (b) See rerf. 5f.
31. Oxazaborolidines 1b and 1c were synthesized according to the literature procedure (see ref. 3).
32. -1. (10) For examples of additive or temperature-induced reversal of stereoinduction, see: (a) Trost, B. M.; Fettes, A.; Shireman, B. T. J. Am. Chem. Soc. 2004, 126, 2660.
33. (b) Casey, C. P.; Martins, S. C.; Fagan, M. A. J. Am. Chem. Soc. 2004, 126, 5585.
34. (c) Arseniyadis, S.; Subhash, P. V.; Valleix, A.; Mathew, S. P.; Blackmond, D. G.; Wagner, A.; Mioskowski, C. J. Am. Chem. Soc. 2005, 127, 6138.