Stereochemical features of oxidative Mannich cyclizations of vinyl- and allyl-silane containing α-silyl-amines and -amides

Tetrahedron Letters

Volumn 37, Issue 5, 1996, Pages 571-574

  Khim, Seock Kyu ^a   Wu, Xiaodong ^a   Mariano, Patrick S ^a  

^a Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030032059     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02263-5     Document Type: Article

References (21)

1. Overman, L E.; Ricca, D. J. Compr. Org. Syn. 1991, 2, 1007.
2. Grieco, P. A.; Fobare, W. F. Tetrahedron Lett. 1986, 27, 5067; J. Chem. Soc. Chem. Commun. 1987, 185.
3. Grieco, P. A.; Fobare, W. F. Tetrahedron Lett. 1986, 27, 5067; J. Chem. Soc. Chem. Commun. 1987, 185.
4. Zhang, X.; Jung. Y. S.; Mariano, P. S.; Fox, M. A.; Martin, P. S.; Merkert, J. Tetrahedron Lett. 1993, 34, 5239.
5. Overman, L. E. Lect. Heterocycl. Chem., 1985, 8, 59; Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857.
6. Overman, L. E. Lect. Heterocycl. Chem., 1985, 8, 59; Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986, 86, 857.
7. Castro, P.; Overman, L. E.; Zhang, X.; Mariano, P. S. Tetrahedron Lett. 1993, 34, 5243.
8. Xu, W.; Zhang, X.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8863; Jeon, Y. T.; Lee, C. P.; Mariano, P. S. J. Am. Chem. Soc., 1991 113, 8847; Yoon, U. C.; Mariano, P. S. Acc. Chem. Res., 1992 25, 233.
9. Xu, W.; Zhang, X.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8863; Jeon, Y. T.; Lee, C. P.; Mariano, P. S. J. Am. Chem. Soc., 1991 113, 8847; Yoon, U. C.; Mariano, P. S. Acc. Chem. Res., 1992 25, 233.
10. Xu, W.; Zhang, X.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8863; Jeon, Y. T.; Lee, C. P.; Mariano, P. S. J. Am. Chem. Soc., 1991 113, 8847; Yoon, U. C.; Mariano, P. S. Acc. Chem. Res., 1992 25, 233.
11. Zhang, X.; Yeh, S. R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211; d'Alessandro, N.; Albini, A.; Mariano, P. S. J. Org. Chem. 1993, 58, 937.
12. Zhang, X.; Yeh, S. R.; Hong, S.; Freccero, M.; Albini, A.; Falvey, D. E.; Mariano, P. S. J. Am. Chem. Soc. 1994, 116, 4211; d'Alessandro, N.; Albini, A.; Mariano, P. S. J. Org. Chem. 1993, 58, 937.
13. Overman, L E.; Kakimoto, M.; Okazaki, M. E.; Meier, G. P. J. Am. Chem. Soc. 1983, 105, 6622; Jacobsen, E. J.; Levin, J.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4329.
14. Overman, L E.; Kakimoto, M.; Okazaki, M. E.; Meier, G. P. J. Am. Chem. Soc. 1983, 105, 6622; Jacobsen, E. J.; Levin, J.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4329.
15. (a) Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097;
16. (b) McCann, S. F.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6107; see also Overman L. E.; Burk, R. M. Tetrahedron Lett. 1984, 25, 5739.
17. (b) McCann, S. F.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6107; see also Overman L. E.; Burk, R. M. Tetrahedron Lett. 1984, 25, 5739.
18. Overman, L. E.; Goldstein, S. W. J. Am. Chem. Soc. 1984, 106, 5360.
19. Speckamp, W. N.; Heimstra, H. Tetrahedron 1985, 41, 4367.
20. A typical method for making N-acyliminium cations employs a sequence beginning with imide reduction to produce an amidol and acid catalyzed elimination.
21. This work was supported by a grant from the National Institutes of Health (GM-27251). We thank Professor Larry Overman for informative discussions about this investigation.