A Stereoselective Cyclization Strategy for the Preparation of γ-Lactams and Their Use in the Synthesis of α-Methyl-β-Proline

Authors

Souvik Banerjee, University of Southern Mississippi
Justin Smith, University of Southern Mississippi
Jillian Smith, University of Southern Mississippi
Caleb Faulkner, University of Southern Mississippi
Douglas S. Masterson, University of Southern MississippiFollow

Document Type

Article

Publication Date

12-7-2012

Department

Chemistry and Biochemistry

Abstract

A straightforward stereoselective and enantiodivergent cyclization strategy for the construction of γ-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 γ-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

Recommended Citation

Banerjee, S., Smith, J., Smith, J., Faulkner, C., Masterson, D. S. (2012). A Stereoselective Cyclization Strategy for the Preparation of γ-Lactams and Their Use in the Synthesis of α-Methyl-β-Proline. Journal of Organic Chemistry, 77(23), 10925-2202.
Available at: https://aquila.usm.edu/fac_pubs/7565