Title

Efficient Access To 3-substituted-gamma-hydroxylactams: The Uncatalyzed Addition Of Diorganozinc Reagents To Cyclic Imides With Heterocyclic Substitution

Document Type

Article

Publication Date

3-5-2014

Abstract

A range of 3-substituted-gamma-hydroxylactams have been prepared via the uncatalyzed addition of organo-zinc nucleophiles to cyclic imides. This reactivity is primarily limited to imides containing heterocyclic N-substitution, but proceeds efficiently with a variety of diorganozinc reagents, including those prepared and utilized without purification, as well as organozinc halides. It is hypothesized that the presence of a Lewis basic directing group is required for optimum reactivity. (C) 2014 Elsevier Ltd. All rights reserved.