Rules for ring closure. Stereoelectronic control in the endocyclic alkylation of ketone enolates

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 7, 1977, Pages 233-235

  Baldwin, Jack E ^a   Kruse, Lawrence I ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049098529     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39770000233     Document Type: Article

References (16)

1. J. E. Baldwin, J.C.S. Chem. Comm., 1976, 734.
2. J. E. Baldwin, J. Cutting, W. Dupont, L. I. Kruse, L. Silberman, and R. C. Thomas, J.C.S. Chem. Comm., 1976, 736.
3. Prepared by method of M. A. Schexnayder and P. S. Engel, J. Amer. Chem. Soc., 1975, 97, 4825.
4. R. Gelin, S. Gelin, and C. Deshayes, Bull. Soc. chim. France, 1973, 2153.
5. R. E. Ireland and J. A. Marshall, J. Org. Chem., 1962, 27, 1615.
6. S. Julia and C. Gueremy, Bull. Soc. chim. France, 1965, 2994.
7. The literature contains two cases wherein attempted closures of enolates of the type (10) led only to enol ether products: G. Baddeley, E. K. Baylis, and B. G. Heaton, Proc. Chem. Soc., 1961, 451.
8. D. Taub, R. D. Hoffsommer, and N. L. Wendler, J. Org. Chem., 1964, 29, 3486.
9. We thank Professor P. Grieco for bringing these results to our attention. A case of a 6-Endo-alkylation has been reported: H. Marschall, K. Tantau, and P. Weyerstahl, Chem. Ber., 1974, 107, 887.
10. E. Wenkert and D. P. Strike, J. Org. Chem., 1962, 27, 1883.
11. K. D. Klenkmöller, H. Marschall, and P. Weyerstahl, Chem. Ber., 1975, 108, 191.
12. H. Marschall and W. B. Mühlenkamp, Chem. Ber., 1976, 109, 2785.
13. A. S. Kende, Org. Reactions, 1960, 11, 261.
14. H. O. House and G. A. Frank, J. Org. Chem., 1965, 30, 2948.
15. F. G. Bordwell, R. C. Scamehorn, and W. R. Springer, J. Amer. Chem. Soc., 1969, 91, 2087.
16. H. O. House, ‘Modern Synthetic Reactions,’ 2nd edn., Benjamin, California, 1972, p. 492.