Diastereoselective Enolsilane Coupling Reactions

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5680-5681

  Miller, Scott J ^a   Bayne, Christopher D ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001387733     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971050y     Document Type: Article

References (23)

1. (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Syntheis:Additions to C-X π-Bonds; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon: New York, 1991; Part 2, pp 99-131.
2. (b) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; vol. 3, Chap. 2.
3. (c) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-115.
4. For representative examples, see: (a) Ito, Y.; Konoike, T.; Harada, T.; Saegusa, T. J. Am. Chem. Soc. 1975, 97, 2912-2914.
5. For more recent representative contributions, see (b) Matsumura, Y.; Nishimura, M.; Hiu, H.; Watanabe, M.; Kise, N. J. Org. Chem. 1996, 61, 2809-2812. (c) Paquette, L. A.; Bzowej, E. I.; Branan, B. M.; Stanton, K. J. J. Org. Chem. 1995, 60, 7277-7283. (d) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457-4460.
6. For more recent representative contributions, see (b) Matsumura, Y.; Nishimura, M.; Hiu, H.; Watanabe, M.; Kise, N. J. Org. Chem. 1996, 61, 2809-2812. (c) Paquette, L. A.; Bzowej, E. I.; Branan, B. M.; Stanton, K. J. J. Org. Chem. 1995, 60, 7277-7283. (d) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457-4460.
7. For more recent representative contributions, see (b) Matsumura, Y.; Nishimura, M.; Hiu, H.; Watanabe, M.; Kise, N. J. Org. Chem. 1996, 61, 2809-2812. (c) Paquette, L. A.; Bzowej, E. I.; Branan, B. M.; Stanton, K. J. J. Org. Chem. 1995, 60, 7277-7283. (d) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457-4460.
8. Magedov, I. V.; Smushkevich, Y. I. J. Chem. Soc., Chem. Commun. 1990, 1686-1687.
9. (a) Endo, Y.; Shudo, K. Tetrahedron Lett. 1991, 32, 4517-4520.
10. (b) Endo, Y.; Shudo, K. Heterocycles 1992, 33, 91-95.
11. (c) Uchida, T.; Endo, Y.; Hizazate, S.; Shudo, K. Chem. Pharm. Bull. 1994, 42, 419-421.
12. (d) Endo, Y.; Uchida, T.; Hizazate, K; Shudo, K. Synthesis 1994, 1096-1105.
13. For reviews of hetero-[3,3]-rearrangements, see: (a) Blechert, S. Synthesis 1989, 71-82. (b) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452. (c) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579-586.
14. For reviews of hetero-[3,3]-rearrangements, see: (a) Blechert, S. Synthesis 1989, 71-82. (b) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452. (c) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579-586.
15. For reviews of hetero-[3,3]-rearrangements, see: (a) Blechert, S. Synthesis 1989, 71-82. (b) Ziegler, F. E. Chem. Rev. 1988, 88, 1423-1452. (c) Overman, L. E. Angew. Chem., Int. Ed. Engl. 1984, 23, 579-586.
16. 3 solution. The organic layer was then vigorously stirred for 10 min in the presence of 1 N HCl. Concentration of the aqueous layer then afforded the pure cyclic hydrazide salt (5a and 5b). See Supporting Information for details.
17. For a review highlighting selectivity issues in [3,3]-sigmatropic rearrangements, see: Enders, D.; Knopp, M.; Schiffers, R. Tetrahedron: Asymmetry 1996, 7, 1847-1882.
18. The relative stereochemical relationships were established on the basis of the characteristically smaller coupling constant between the C3 and C4 methine protons in the trans-products. For example, see: Tschappat, K. D.; Crider, A. M.; Hassan, M. N.; Fahn, S. J. Heterocycl. Chem. 1987, 24, 673-676.
19. In this case, stereochemical assignment was made based on the large coupling constants observed for the vicinal protons. See Supporting Information for details.
20. Conversion of α-azido carbonyl compounds to the corresponding diketones by a related mechanism has been reported. See: (a) Edwards, O. E.; Purushothaman, K. K. Can. J. Chem. 1964, 42, 712-716. (b) Manis, P. A.; Rathke, M. W. J. Org. Chem. 1980, 45, 4952-4954.
21. Conversion of α-azido carbonyl compounds to the corresponding diketones by a related mechanism has been reported. See: (a) Edwards, O. E.; Purushothaman, K. K. Can. J. Chem. 1964, 42, 712-716. (b) Manis, P. A.; Rathke, M. W. J. Org. Chem. 1980, 45, 4952-4954.
22. (a) Doering, W. v. E.; Roth, W. R. Angew. Chem., Int. Ed. Engl. 1963, 2, 115-122.
23. (b) Reference 7 and references cited therein.