N-Heterocyclic Carbene Catalyzed Umpolung of Michael Acceptors for Intermolecular Reactions

Biju, Akkattu T. ; Padmanaban, Mohan ; Wurz, Nathalie E. ; Glorius, Frank (2011) N-Heterocyclic Carbene Catalyzed Umpolung of Michael Acceptors for Intermolecular Reactions Angewandte Chemie International Edition, 50 (36). pp. 8412-8415. ISSN 14337851

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Official URL: http://doi.org/10.1002/anie.201103555

Related URL: http://dx.doi.org/10.1002/anie.201103555

Abstract

The N-heterocyclic carbene catalyzed umpolung of Michael acceptors proceeds through the formation of a deoxy-Breslow intermediate (see scheme; EWG=electron-withdrawing group). This nucleophilic species can react with other Michael acceptors in an intermolecular fashion, thereby resulting in the formation of homo- or heterodimeric olefins. This “Michael umpolung” should become a valuable method for the formation of densely functionalized olefins.

Item Type:Article
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ID Code:128725
Deposited On:03 Nov 2022 06:56
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