Catalytic additions of acylsilanes to imines: An acyl anion strategy for the direct synthesis of α-amino ketones

Organic Letters

Volumn 6, Issue 23, 2004, Pages 4363-4366

  Mattson, Anita E ^a   Scheidt, Karl A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; KETONE DERIVATIVE; SILANE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 9444255109     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0481129     Document Type: Article

References (37)

1. (a) Di Gioia, M. L.; Leggio, A.; Liguori, A.; Napoli, A.; Siciliano, C.; Sindona, G. J. Org. Chem. 2001, 66, 7002-7007 and references therein.
2. (c) Beguin, C.; Andurkar, S. V.; Jin, A. Y.; Stables, J. P.; Weaver, D. F.; Kohn, H. Bioorg. Med. Chem. 2003, 11, 4275-4285.
3. (d) Haustein, K. O. Int. J. Clin. Pharm. Ther. 2003, 41, 56-66.
4. (a) Sorrell, T. N.; Allen, W. E. J. Org. Chem. 1994, 59, 1589-1590.
5. (b) Langer, P.; Bodtke, A. Tetrahedron Lett. 2003, 44, 5965-5967.
6. (c) Frantz, D. E.; Morency, L.; Soheili, A.; Murry, J. A.; Grabowski, E. J. J.; Tillyer, R. D. Org. Lett. 2004, 6, 843-846.
7. For reviews on the utility and synthesis of 1,2-amino alcohols from α-amino ketones, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. (b) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546.
8. For reviews on the utility and synthesis of 1,2-amino alcohols from α-amino ketones, see: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875. (b) Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546.
9. (a) Yet, L. Angew. Chem., Int. Ed. 2001, 40, 875-877.
10. For recent enantioselective variants, see: (b) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279-1281. (c) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634-5635 and references therein.
11. For recent enantioselective variants, see: (b) Sigman, M. S.; Vachal, P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2000, 39, 1279-1281. (c) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634-5635 and references therein.
12. For examples of this strategy utilizing acylimines generated in situ, see: (a) Castells, J.; López-Calahorra, F.; Bassedas, M.; Urrios, P. Synthesis 1988, 314-315. (b) Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696-9697.
13. For examples of this strategy utilizing acylimines generated in situ, see: (a) Castells, J.; López-Calahorra, F.; Bassedas, M.; Urrios, P. Synthesis 1988, 314-315. (b) Murry, J. A.; Frantz, D. E.; Soheili, A.; Tillyer, R.; Grabowski, E. J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123, 9696-9697.
14. (a) Grobel, B. T.; Seebach, D. Synthesis 1977, 357-402.
15. (b) Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239-258.
16. (c) Johnson, J. S. Angew. Chem., Int. Ed. 2004, 43, 1326-1328.
17. (a) Mattson, A. E.; Bharadwaj, A. R.; Scheidt, K. A. J. Am. Chem. Soc. 2004, 126, 2314-2315.
18. (b) Bharadwaj, A. R.; Scheidt, K. A. Org. Lett. 2004, 6, 2465-2468.
19. For additional recent investigations of acylsilanes as acyl anions, see: (c) Xin, L. H.; Johnson, J. S. Angew. Chem., Int. Ed. 2003, 42, 2534-2536. (d) Xin, L. H.; Potnick, J. R.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 3070-3071.
20. For additional recent investigations of acylsilanes as acyl anions, see: (c) Xin, L. H.; Johnson, J. S. Angew. Chem., Int. Ed. 2003, 42, 2534-2536. (d) Xin, L. H.; Potnick, J. R.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 3070-3071.
21. (a) Krzyzanowska, B.; Stec, W. J. Synthesis 1982, 270-273.
22. (b) Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561-5568. For recent examples of N-phosphinoyl imines in enantioselective reactions, see ref 4c and references therein. Less activated azomethines (e.g., N-benzylimines) afforded no conversion.
23. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
24. Mecozzi, T.; Petrini, M. J. Org. Chem. 1999, 64, 8970-8972.
25. (a) Palmer, M. J.; Studley, J. R.; Walsgrove, T. C.; Wills, M. Tetrahedron 1998, 54, 8827-8840.
26. (b) Fraser, D. S.; Park, S. B.; Chong, J. M. Can. J. Chem. 2004, 82, 87-101. See the Supporting Information for reaction details.
27. For a review of thiamine-catalyzed processes, see: Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5289-5295. For a mechanistic discussion of thiazolium salts in the related benzoin reaction, see: (a) Breslow, R.; Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242. (b) White, M. J.; Leeper, F. J. J. Org. Chem. 2001, 66, 5124-5131.
28. For a review of thiamine-catalyzed processes, see: Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5289-5295. For a mechanistic discussion of thiazolium salts in the related benzoin reaction, see: (a) Breslow, R.; Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242. (b) White, M. J.; Leeper, F. J. J. Org. Chem. 2001, 66, 5124-5131.
29. For a review of thiamine-catalyzed processes, see: Pohl, M.; Lingen, B.; Müller, M. Chem. Eur. J. 2002, 8, 5289-5295. For a mechanistic discussion of thiazolium salts in the related benzoin reaction, see: (a) Breslow, R.; Schmuck, C. Tetrahedron Lett. 1996, 37, 8241-8242. (b) White, M. J.; Leeper, F. J. J. Org. Chem. 2001, 66, 5124-5131.
30. (a) Brook, A. G.; LeGrow, G. E.; MacRae, D. M. Can. J. Chem. 1967, 45, 239-253.
31. (b) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
32. (c) Moser, W. H. Tetrahedron 2001, 57, 2065-2084.
33. Replacement of 2-propanol with 3-octanol affords 3-trimethylsilyl- oxyloctane (observed by GC), thus indicating that the alcohol is the silyl group acceptor. See the Supporting Information.
34. An alternate pathway may involve direct addition of II to the imine followed by desilylation to turn over the catalyst and generate the product.
35. 3) when combining acylsilane 6, imine 12, and thiazolium salt 10.
36. Barletta, G. L.; Zou, Y.; Huskey, W. P.; Jordan, F. J. Am. Chem. Soc. 1997, 119, 2356-2362.
37. See references 7a and 7b.