Title

A Stereoselective Cyclization Strategy for the Preparation of gamma-Lactams and Their Use in the Synthesis of alpha-Methyl-beta-Proline

Document Type

Article

Publication Date

12-7-2012

Department

Chemistry and Biochemistry

Abstract

A straightforward stereoselective and enantiodivergent cyclization strategy for the construction of gamma-lactams is described. The cyclization strategy makes use of chiral malonic esters prepared from enantiomerically enriched monoesters of disubstituted malonic acid. The cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. A Hammett study illustrates that the cyclization is under electronic control. The resulting gamma-lactam can be readily converted into a novel proline analogue.

Publication Title

JOURNAL OF ORGANIC CHEMISTRY

Volume

77

Issue

23

First Page

10925

Last Page

2202