Tetrahedron Letters

Efficient access to 3-substituted-γ-hydroxylactams: the uncatalyzed addition of diorganozinc reagents to cyclic imides with heterocyclic substitution

KS DeGlopper, JM Dennis, JB Johnson

Index: Deglopper, Kimberly S.; Dennis, Joseph M.; Johnson, Jeffrey B. Tetrahedron Letters, 2014 , vol. 55, # 10 p. 1843 - 1845

Full Text: HTML

Citation Number: 1

Abstract

Abstract A range of 3-substituted-γ-hydroxylactams have been prepared via the uncatalyzed addition of organozinc 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 ...