Synthesis 2007(8): 1179-1184  
DOI: 10.1055/s-2007-965981
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of 3,4-trans-Disubstituted γ-Lactams by Cerium(IV) Ammonium Nitrate Mediated Radical Cyclization of Cinnamamides

Vijay Nair*, Kishor Mohanan, Tachapully D. Suja, Akkattu T. Biju
Organic Chemistry Section, Regional Research Laboratory (CSIR), Trivandrum 695019, India
Fax: +91(471)2491712; e-Mail: vijaynair_2001@yahoo.com;
Further Information

Publication History

Received 9 January 2007
Publication Date:
12 March 2007 (eFirst)

Abstract

A facile synthesis of 3,4-trans-disubstituted γ-lactams was developed, consisting of the radical cyclization of cinnam­amides mediated by cerium(IV) ammonium nitrate. The single-electron-transfer (SET) reaction of the methoxystyrenyl moiety mediated by cerium(IV) ammonium nitrate gives rise to a cation radical, whose cyclization followed by reaction with oxygen and methanol generates 3,4-trans-disubstituted γ-lactams.