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Enantioselective Synthesis of Epoxides Having a Tetrasubstituted Trifluoromethylated Carbon Center: Methylhydrazine‐Induced Aerobic Epoxidation of β,β‐Disubstituted Enones
Author(s) -
Kawai Hiroyuki,
Okusu Satoshi,
Yuan Zhe,
Tokunaga Etsuko,
Yamano Akihito,
Shiro Motoo,
Shibata Norio
Publication year - 2013
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.201209355
Subject(s) - methylhydrazine , chemistry , enantioselective synthesis , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , propellant
The unprecedented title reaction is catalyzed by a methylhydrazine/base/organocatalyst ( 1 ) system. Biologically attractive epoxides ( 2 ) having a tetrasubstituted trifluoromethylated carbon center were obtained with excellent enantioselectivity for the first time. 18 O‐labeling experiments suggest a mechanism involving the activation of molecular oxygen. MTBE=methyl tert ‐butyl ether.