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Highly Enantioselective Organocatalytic Conjugate Addition of Malonates toAcyclic α,β‐Unsaturated Enones
Author(s) -
Halland Nis,
Aburel Pompiliu S.,
Jørgensen Karl Anker
Publication year - 2003
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.200390182
Subject(s) - enantioselective synthesis , conjugate , optically active , chemistry , catalysis , michael reaction , addition reaction , organocatalysis , organic chemistry , combinatorial chemistry , mathematics , mathematical analysis
An imidazolidine easily prepared from phenylalanine is the catalyst for the highly enantioselective Michael addition shown. A great diversity of α,β‐unsaturated enones was transformed with excellent enantioselectivities. The scope of the reaction is further demonstrated by the synthesis of two optically active compounds, a δ‐ketoester and a tetrahydroquinoline (see scheme).
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