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Enantioselective Synthesis of Trifluoromethyl‐Substituted 2‐Isoxazolines: Asymmetric Hydroxylamine/Enone Cascade Reaction
Author(s) -
Matoba Kazutaka,
Kawai Hiroyuki,
Furukawa Tatsuya,
Kusuda Akihiro,
Tokunaga Etsuko,
Nakamura Shuichi,
Shiro Motoo,
Shibata Norio
Publication year - 2010
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.201002065
Subject(s) - enantioselective synthesis , hydroxylamine , trifluoromethyl , enone , chemistry , enantiomer , cascade , organic chemistry , ketone , catalysis , stereochemistry , combinatorial chemistry , chromatography , alkyl
Cuts both ways : The title reaction consists of an addition/cyclization/dehydration sequence and affords the biologically important chiral 3,5‐diaryl‐5‐(trifluoromethyl)‐2‐isoxazolines 1 in excellent yields with high ee values. The flexibility of accessing either the S or R enantiomers of the products has been achieved by the appropriate choice of phase‐transfer catalyst ( 2 ).