N‐Heterocyclic Carbene Catalyzed Umpolung of Michael Acceptors for Intermolecular Reactions | Zendy

Biju Akkattu T. | Zendy; Padmanaban Mohan | Zendy; Wurz Nathalie E. | Zendy; Glorius Frank | Zendy

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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.

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