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NHC‐Catalyzed Michael Addition to α,β‐Unsaturated Aldehydes by Redox Activation
Author(s) -
De Sarkar Suman,
Studer Armido
Publication year - 2010
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.201004593
Subject(s) - umpolung , reactivity (psychology) , electrophile , nucleophile , chemistry , carbene , redox , catalysis , nucleophilic addition , organocatalysis , michael reaction , combinatorial chemistry , organic chemistry , enantioselective synthesis , pathology , medicine , alternative medicine
Through oxidative carbene catalysis the reactivity of enals can be reversed at the β position from the typical electrophilic to nucleophilic (homoenolate chemistry) further to electrophilic reactivity by two consecutive umpolung processes. These redox‐activated Michael acceptors show higher reactivity at the β position than that for the starting enals. Their reactions with β‐dicarbonyl compounds provide dihydropyranones in good to excellent yields under mild conditions.