N-Heterocyclic carbene catalyzed umpolung of michael acceptors for intermolecular reactions

TitleN-Heterocyclic carbene catalyzed umpolung of michael acceptors for intermolecular reactions
Publication TypeJournal Article
Year of Publication2011
AuthorsBiju, AT, Padmanaban, M, Wurz, NE, Glorius, F
JournalAngewandte Chemie-International Edition
Volume50
Issue36
Pagination8412-8415
Date PublishedAUG
ISSN1433-7851
Keywordscarbenes, Michael acceptors, nitrogen heterocycles, organocatalysis, umpolung
Abstract

eahciM! 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.

DOI10.1002/anie.201103555
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

9.24

Divison category: 
Organic Chemistry