Enantioselective Synthesis of Trifluoromethyl‐Substituted 2‐Isoxazolines: Asymmetric Hydroxylamine/Enone Cascade Reaction | Zendy

Matoba Kazutaka | Zendy; Kawai Hiroyuki | Zendy; Furukawa Tatsuya | Zendy; Kusuda Akihiro | Zendy; Tokunaga Etsuko | Zendy; Nakamura Shuichi | Zendy; Shiro Motoo | Zendy; Shibata Norio | Zendy

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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 ).

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