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 ; Biju, Akkattu (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 0039-7881

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

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 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.

Item Type:Article
Source:Copyright of this article belongs to Georg Thieme Verlag KG
Keywords:cerium(IV) ammonium nitrate, intramolecular cyclization, cinnamamides, single electron transfer, γ-lactams
ID Code:128744
Deposited On:03 Nov 2022 06:57
Last Modified:03 Nov 2022 06:57

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