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
Recommended Citation
DeGlopper, Kimberly S., Joseph M. Dennis, and Jeffrey B. Johnson. “Efficient Access to 3-Substituted-Γ-Hydroxylactams: The Uncatalyzed Addition of Diorganozinc Reagents to Cyclic Imides with Heterocyclic Substitution.” Tetrahedron Letters 55, no. 10 (March 5, 2014): 1843–45. doi:10.1016/j.tetlet.2014.01.130.
