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An Unexpected Organocatalytic Asymmetric Tandem Michael/Morita–Baylis–Hillman Reaction
Author(s) -
Cabrera Silvia,
Alemán José,
Bolze Patrick,
Bertelsen Søren,
Jørgensen Karl Anker
Publication year - 2007
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.200704076
Subject(s) - baylis–hillman reaction , organocatalysis , amine gas treating , tandem , michael reaction , chemistry , catalysis , trimethylsilyl , optically active , cascade reaction , combinatorial chemistry , organic chemistry , enantioselective synthesis , materials science , composite material
Simply complex : An organocatalytic tandem Michael/Morita–Baylis–Hillman reaction has been developed in which secondary amine catalysts allow for a very selective, scalable synthesis of highly substituted optically active cyclohexanones (see scheme, TMS=trimethylsilyl). Mechanistic studies indicate an active role of the secondary amine catalyst in the Morita–Baylis–Hillman reaction.