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N‐Heterocyclic Carbene Catalyzed Umpolung of Michael Acceptors for Intermolecular Reactions
Author(s) -
Biju Akkattu T.,
Padmanaban Mohan,
Wurz Nathalie E.,
Glorius Frank
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201103555
Subject(s) - umpolung , carbene , nucleophile , intermolecular force , chemistry , michael reaction , catalysis , combinatorial chemistry , organic chemistry , molecule
leahciM! 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.