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

Publication Source

Tetrahedron Letters

Volume Number

55

Issue Number

10

First Page

1843

Last Page

1845

Publisher

Elsevier

ISSN

0040-4039

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.

Keywords

Imides, Organozinc Reagents, Nucleophilic Addition, Directing Groups, Bond Activation, Radical Cyclization, Organic-synthesis, C-h, Catalysis, Functionalization, Phthalimides, Acylation

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