Preparation of 3?azetidinols with non?bulky 1?alkyl substituents

Robert H. Higgins, Fayetteville State University
Quentin L. Eaton, Fayetteville State University
Leroy Worth, Fayetteville State University
Myra V. Peterson, Fayetteville State University

Abstract

Cyclization of either the tetrahydropyranyl or trimethylsilyl ether of 1?(alkylamino)?3?chloro?2?propanols 1 followed by cleavage of the azetidinyl ether provides a general method for the preparation of 1?alkyl?3?azetidinols. Unhindered amines provide a more facile preparation of derivatives of 1, or its ethers, than do hindered amines, while hindered derivatives of 1 undergo more facile ring closure. Copyright © 1987 Journal of Heterocyclic Chemistry