Stereoselective synthesis of 3,4-trans-disubstituted γ-lactams by Cerium(IV) ammonium nitrate mediated radical cyclization of cinnamamides

Nair, Vijay ; Mohanan, Kishor ; Suja, Tachapully D. ; Biju, Akkattu T. (2007) Stereoselective synthesis of 3,4-trans-disubstituted γ-lactams by Cerium(IV) ammonium nitrate mediated radical cyclization of cinnamamides Synthesis, 2007 (8). pp. 1179-1184. ISSN 1570-2693

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Official URL: https://www.thieme-connect.com/ejournals/abstract/...

Related URL: http://dx.doi.org/10.1055/s-2007-965981

Abstract

A facile synthesis of 3,4-trans-disubstituted γ-lactams was developed, consisting of the radical cyclization of cinnam-amides 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.

Item Type:Article
Source:Copyright of this article belongs to Bohn Stafleu Van Loghum.
Keywords:Cerium(IV) Ammonium Nitrate; Intramolecular Cyclization; Cinnamamides; Single Electron Transfer; γ-lactams
ID Code:84083
Deposited On:24 Feb 2012 06:19
Last Modified:24 Feb 2012 06:19

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