Enantioselective Synthesis of Epoxides Having a Tetrasubstituted Trifluoromethylated Carbon Center: Methylhydrazine‐Induced Aerobic Epoxidation of β,β‐Disubstituted Enones | Zendy

Kawai Hiroyuki | Zendy; Okusu Satoshi | Zendy; Yuan Zhe | Zendy; Tokunaga Etsuko | Zendy; Yamano Akihito | Zendy; Shiro Motoo | Zendy; Shibata Norio | Zendy

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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.

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