An asymmetric oxazoline ketenimine rearrangement. Construction of chiral α-quaternary carbon ketones

Tetrahedron Letters

Volumn 40, Issue 26, 1999, Pages 4765-4768

  Dwyer, Michael P ^a   Price, David A ^a   Lamar, Jason E ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CONFORMATIONAL TRANSITION; SYNTHESIS;

EID: 0033603449     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00729-7     Document Type: Article

References (20)

1. (a) Meyers, A. I.; Romo, D. Tetrahedron 1991, 47, 9503.
2. (b) Fuji, K. Chem. Rev. 1993, 93, 2037.
3. See also an earlier review on quaternary carbon syntheses: (c) Martin, S. F. Tetrahedron 1980, 36, 419.
4. (a) Meyers, A. I.; Smith, E. M. Tetrahedron Lett. 1970, 4355.
5. (b) Meyers, A. I.; Smith, E. M.; Jurjevich, A. F. J. Am. Chem. Soc. 1971, 93, 2314.
6. (c) Meyers, A. I.; Smith, E. M.; Ao, M. S. J. Org. Chem. 1973, 38, 2129.
7. (d) Meyers, A. I.; Kovelesky, A. C.; Jurjevich, A. F. J. Org. Chem. 1973, 38, 2136.
8. Dubois, J. E.; Lion, C. R. Acad. Sci. 1972, 274, 203.
9. Marko, I.; Ronsmans, B.; Hesbain-Frisque, A.-M.; Dumas, S.; Ghosez, L.; Ernst, B.; Greuter, H. J. Am. Chem. Soc. 1985, 107, 2192.
10. For reviews of ketenimines in synthesis, see: (a) Krow, G. R. Angew. Chem., Int. Ed. 1971, 10, 435.
11. (b) Michael, J. P.; De Koning, C. B. Ketenimines and their P, As, Sb, and Bi analogues; in Comprehensive Organic Functional Group Transformations; Pattenden, G., Ed.; Elsevier: Tarrytown, New York, 1995; Vol 3, pp. 555-610.
12. For related examples, see: (c) Hiroi, K.; Sato, S. Chem. Pharm. Bull. 1985, 33, 2331.
13. (d) Hiroi, K.; Sato, S. Chem. Pharm. Bull. 1985, 33, 4691.
14. (a) Meyers, A. I.; Knaus, G. J. Am. Chem. Soc. 1974, 96, 6508.
15. (b) Meyers, A. I.; Knaus, G.; Kamata, K.; Ford, M. E. J. Am. Chem. Soc. 1976, 98, 567.
16. 6 by integrating the methyl signals of the TMS ketenimine.
17. For examples of thermal equilibration of metalloenamines, see: (a) Meyers, A. I.; Williams, D. R.; Erickson, G. W.; White, S.; Druelinger, M. J. Am. Chem. Soc. 1981, 103, 3081.
18. (b) Meyers, A. I.; Williams, D. R.; White, S.; Erickson, G. W. J. Am. Chem. Soc. 1981, 103, 3088.
19. Lee, J. Y; Lynch, T. J.; Mao, D. T.; Bergbeiter, D. E.; Newcomb, M. J. Am. Chem. Soc. 1981, 103, 6215.
20. Meyers, A. I.; Williams, D. R.; Druelinger, M. J. Am. Chem. Soc. 1976, 98, 3032.