Premium
Enantioselective Michael Addition to α,β‐Unsaturated Imides Catalyzed by a Bifunctional Organocatalyst
Author(s) -
Hoashi Yasutaka,
Okino Tomotaka,
Takemoto Yoshiji
Publication year - 2005
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.200500459
Subject(s) - bifunctional , thiourea , moiety , michael reaction , malononitrile , chemistry , enantioselective synthesis , aryl , alkyl , adduct , catalysis , organocatalysis , organic chemistry , addition reaction , combinatorial chemistry
High enantioselectivities (up to 94 % ee ) were attained in the Michael addition of a variety of α,β‐unsaturated imides 1 and malononitrile ( 2 ) catalyzed by bifunctional thiourea 4 . The pyrrolidinone moiety of 1 plays a key role in the reaction. The reaction provides access to a variety of Michael adducts 3 (see scheme; R=aryl and alkyl groups).