Synthesis of Chiral α,α-Disubstituted Cyclic Nitrones from Secondary Lactams

Abstract

Abstract Synthesis of chiral α,α-disubstituted cyclic nitrones from secondary lactams is reported. The method consists of two stages involving N-oxidation of the lactams and nucleophilic addition to the lactam carbonyls. The N-oxidation of secondary lactams with mCPBA via imidates provides cyclic nitrones with a chiral stereocenter adjacent to the nitrogen atom. A variety of α,α-disubstituted cyclic nitrones were quickly obtained simply by changing organolithium reagents in the nucleophilic addition to N-OSEM lactams.