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Highly Regio‐ and Stereoselective Double Michael Addition–Cyclization of 2,3‐Allenoates with Organozinc Compounds: Efficient Synthesis of 5‐Benzylidenecyclohex‐2‐enones
Author(s) -
Lu Zhan,
Chai Guobi,
Ma Shengming
Publication year - 2008
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.200801497
Subject(s) - stereocenter , stereoselectivity , racemization , michael reaction , chemistry , stereochemistry , regioselectivity , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis
Highly substituted α,β‐unsaturated cyclohexenones, a key structural motif in many natural products, were prepared in the title reaction (see scheme). High diastereoselectivity was observed with respect to the two stereogenic centers at the 4‐ and 6‐positions. When optically active starting materials were used, the desired products were formed without evident racemization. A rationale for the observed stereoselectivity is proposed.