Organic Chemistry Portal

Abstracts

Search:

Addition Reactions of Iodomethyllithium to Imines. A Direct and Efficient Synthesis of Aziridines and Enantiopure Amino Aziridines

José M. Concellón*, Humberto Rodríguez-Solla and Carmen Simal

*Departamento de Química Orgánica e Inorgánica, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain, Email: jmcguniovi.es

J. M. Concellón, H. Rodríguez-Solla, C. Simal, Org. Lett., 2008, 10, 4457-4460.

DOI: 10.1021/ol801607r (free Supporting Information)


see article for more reactions

Abstract

The reaction of N-tosyl imines with in situ generated iodomethyllithium, with a simple and rapid experimental protocol, allows an efficient and general synthesis of aziridines. A reaction of a chiral aldimine derived from phenylalaninal proceeded with high diastereoselectivity. A mechanism to explain this novel reaction is proposed.

see article for more examples


proposed mechanism



Key Words

Aziridines


ID: J54-Y2008-2850