Preparation and Epoxidation of Conjugated Lactams: Influence of Ring Size on Epoxidation

作者: Bing Li , Michael B. Smith

DOI: 10.1080/00397919508012690

关键词:

摘要: Abstract α,β-Epoxy-lactams can be prepared from conjugated lactams by treatment with m-chloroperoxybenzoic acid. Good yields are obtained, however, only 2-pyrrolidinone derivatives. The yield of epoxy-lactam diminishes dramatically as the size lactam ring increases.

参考文章(6)
Deborah A. Davis, Gordon W. Gribble, A regioselective diels-alder synthesis of ellipticine Tetrahedron Letters. ,vol. 31, pp. 1081- 1084 ,(1990) , 10.1016/S0040-4039(00)88731-6
Paul F. Keusenkothen, Michael B. Smith, Asymmetric synthesis of pyrrolizidinones by radical cyclization of N-allylic pyroglutamates Tetrahedron Letters. ,vol. 30, pp. 3369- 3372 ,(1989) , 10.1016/S0040-4039(00)99247-5
Paul F. Keusenkothen, Michael B. Smith, Asymmetric radical cyclizations: the synthesis of 6-Alkyl Pyrrolizidin-2-ones Tetrahedron. ,vol. 48, pp. 2977- 2992 ,(1992) , 10.1016/S0040-4020(01)92242-2
Melvin L. Rueppel, Henry Rapoport, Oxidation of .alpha.-ketoacyl derivatives. Rearrangement of pyruvates to malonates Journal of the American Chemical Society. ,vol. 94, pp. 3877- 3883 ,(1972) , 10.1021/JA00766A036
P. A. Zoretic, P. Soja, SULFENYLATION AND SELENENYLATION OF LACTAMS Journal of Organic Chemistry. ,vol. 41, pp. 3587- 3589 ,(1976) , 10.1021/JO00884A022
Yasufumi Ohfune, Masako Tomita, Total synthesis of (-)-domoic acid. A revision of the original structure Journal of the American Chemical Society. ,vol. 104, pp. 3511- 3513 ,(1982) , 10.1021/JA00376A048