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Organocascade Reactions of Enones Catalyzed by a Chiral Primary Amine
Author(s) -
Wu LiYuan,
Bencivenni Giorgio,
Mancinelli Michele,
Mazzanti Andrea,
Bartoli Giuseppe,
Melchiorre Paolo
Publication year - 2009
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.200903280
Subject(s) - amine gas treating , primary (astronomy) , cyclohexane , catalysis , chemistry , combinatorial chemistry , sequence (biology) , organic chemistry , physics , biochemistry , astronomy
Primary amines do it differently : Acyclic α,β‐unsaturated ketones are activated toward a characteristic stepwise double‐Michael addition sequence by chiral primary amine catalysis, which offers a powerful alternative in the design of synthetically useful organocascade reactions (see scheme, EWG=electron‐withdrawing group). This method complements the Diels–Alder reaction for the one‐step synthesis of complex cyclohexane scaffolds with excellent optical purity.