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Synthesis of Functionalized Cyclopentenes through Catalytic Asymmetric [3+2] Cycloadditions of Allenes with Enones
Author(s) -
Wilson Jonathan E.,
Fu Gregory C.
Publication year - 2006
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.200503312
Subject(s) - stereocenter , enantioselective synthesis , chemistry , catalysis , variety (cybernetics) , scheme (mathematics) , structural isomer , stereochemistry , combinatorial chemistry , organic chemistry , computer science , mathematics , artificial intelligence , mathematical analysis
A phosphepine catalyst mediates enantioselective [3+2] cycloadditions of allenes with a variety of β‐substituted α,β‐unsaturated enones to produce highly functionalized cyclopentenes that contain two contiguous stereocenters (see scheme). Surprisingly, opposite regioisomers are produced as compared to reactions with β‐unsubstituted enones.