Proline-based N-oxides as readily available and modular chiral catalysts. Enantioselective reactions of allyltrichlorosilane with aldehydes

Organic Letters

Volumn 7, Issue 15, 2005, Pages 3151-3154

  Traverse, John F ^a   Zhao, Yu ^a   Hoveyda, Amir H ^a   Snapper, Marc L ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; AMINE OXIDE; DRUG DERIVATIVE; PROLINE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

ALCOHOLS; ALDEHYDES; CATALYSIS; CYCLIC N-OXIDES; MOLECULAR STRUCTURE; PROLINE; SILANES; STEREOISOMERISM; TEMPERATURE;

EID: 23044493928     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050814q     Document Type: Article

References (42)

1. For recent reviews, see: (a) Berkessel, A.; Gröger, H.; MacMillan, D. Asymmetric Organocatalysis: From Biomimetic Concepts to Applications in Asymmetric Synthesis; Wiley-VCH: Weinheim, 2005; pp 1-454.
2. (b) Hoveyda, A. H.; Hird, A. W.; Kacprzynski, M. A. Chem. Commun. 2004, 1779-1785.
3. (c) Miller, S. J. Acc. Chem. Res. 2004, 37, 601-610.
4. (d) Groeger, H.; Wilken, J.; Berkessel, A. Org. Synth. Highlights V 2003, 178-186.
5. For a discussion, see: Hoveyda, A. H. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.: Wiley-VCH: Weinheim, 2002; pp 991-1016.
6. For representative examples, see: (a) Cole, B. M.; Shimizu, K. D.; Krueger, C. A.; Harrity, J. P. A.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 1996, 35, 1668-1671.
7. (b) Krueger, C. A.; Kuntz, K. W.; Dzierba, C. D.; Wirschun, W. G.; Gleason, J. D.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 4284-4285.
8. (c) Luchaco-Cullis, C. A.; Mizutani, H.; Murphy, K. E.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2001, 40, 1456-1460.
9. (d) Degrado, S. J.; Mizutani, H.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 755-756.
10. (e) Akullian, L. C.; Snapper, M. L.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4244-4247.
11. (f) Josephsohn, N. S.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 3734-3735.
12. (a) O'Neil, I. A.; Turner, C. D.; Kalindjian, S. B. Synlett 1997, 777-780.
13. (b) Tao, B.; Lo, M. M-C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 353-354.
14. (c) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233-4235.
15. (d) Shimada, T.; Kina, A.; Ikeda, S.; Hayashi, T. Org. Lett. 2002, 4, 2799-2801.
16. (e) Malkov, A. V.; Orsini, M.; Pernazza, D.; Muir, K. W.; Langer, V.; Meghani, P.; Kocovsky, P. Org. Lett. 2002, 4, 1047-1049.
17. (f) Malkov, A. V.; Bell, M.; Orsini, M.; Parnazza, D.; Massa, A.; Herrmann, P.; Meghani, P.; Kocovsky, P. J. Org. Chem. 2003, 68, 9659-9668.
18. (g) Malkov, A. V.; Dufkova, L.; Farrugia, L.; Kocovsky, P. Angew. Chem., Int. Ed. 2003, 42, 3674-3677.
19. (h) Shimada, T.; Kina, A.; Hayashi, T. J. Org. Chem. 2003, 68, 6329-6337.
20. (i) Kina, A.; Shimada, T.; Hayashi, T. Adv. Synth. Catal. 2004, 346, 1169-1174.
21. For representative examples, see: (a) Gung, B. W.; Xue, X.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 10692-10697.
22. (b) Racherla, U. S.; Liao, Y.; Brown, H. C. J. Org. Chem. 1992, 57, 6614-6617.
23. Duthaler, R.; Hafner, A.; Bold, G. Chem. Rev. 1992, 92, 807-832.
24. For select examples, see: (a) Kubota, K.; Leighton, J. L. Angew. Chem., Int. Ed. 2003, 43, 946-948.
25. (b) Kinnard, J. W. A.; Ng, P. Y.; Kubota, K.; Wang, X.; Leighton, J. L. J. Am. Chem. Soc. 2002, 124, 7920-7921.
26. For representative examples, see: (a) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724.
27. (b) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200.
28. (c) Lu, J.; Hong, M.-L.; Ji, S.-J.; Loh, T.-P. Chem. Commun. 2005, 1010-1012 and references therein.
29. (a) Furuta, K.; Mouri, M.; Yamamoto, H. Synlett 1991, 561-563.
30. (b) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490-11495.
31. (c) Gauthier, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1996, 35, 2363-2365.
32. (d) Bode, J. W.; Gauthier, D. R.; Carreira, E. M. Chem. Commun. 2001, 2560-2561.
33. (a) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763-2794.
34. (b) Masse, C. E.; Panek, J. S. Chem. Rev. 1995, 95, 1293-1316.
35. For a review of pyridine N-oxides as chiral catalysts, see: Chelucci, G.; Murineddu, G.; Pinna, G. A. Tetrahedron: Asymmetry 2004, 15, 1373-1389.
36. O'Neil, I. A.; Potter, A. J. Chem. Commun. 1998, 1487-1488 and references therein.
37. For a review of directed reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1306-1360.
38. Catalysts bearing a secondary amide with the indicated relative stereochemistry were selected, since the intramolecular H-bonding between the amide and N-oxide is reported to be critical to stability of these compounds. See: O'Neil, I. A.; Miller, N. D.; Peake, J.; Barkley, J. V.; Low, C. M. R.; Kalindjian, S. B. Synlett 1993, 515-518.
39. 2 gives rise to low conversion and ee. With DMF >98% conversion and <2% ee is observed (see: Kobayashi, S.; Nishio, K. J. J. Org. Chem. 1994, 59, 6620-6628).
40. The lower conversion at higher temperatures can be attributed to loss of catalyst through reduction of the N-oxide; the derived reduced product was isolated in several representative cases.
41. Presumably due to formation of O-silyl chlorohydrins, attempts to effect additions to aliphatic aldehydes were unsuccessful. See: Denmark, S. E.; Fu, J. Org. Lett. 2002, 4, 1951-1953.
42. Cotton, F. A. Advanced Inorganic Chemistry, 5th ed.; John Wiley & Sons: New York, 1988; pp 1299-1300.