Efficient Access to Trifluoromethyl Diarylpyrrolines and their N‐Oxides through Enantioselective Conjugate Addition of Nitromethane to β,β‐Disubstituted Enones | Zendy

Kawai Hiroyuki | Zendy; Yuan Zhe | Zendy; Kitayama Takashi | Zendy; Tokunaga Etsuko | Zendy; Shibata Norio | Zendy

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Efficient Access to Trifluoromethyl Diarylpyrrolines and their N‐Oxides through Enantioselective Conjugate Addition of Nitromethane to β,β‐Disubstituted Enones

Author(s) -

Kawai Hiroyuki,

Yuan Zhe,

Kitayama Takashi,

Tokunaga Etsuko,

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.201301123

Subject(s) - nitromethane , enantioselective synthesis , trifluoromethyl , conjugate , chemistry , aryl , combinatorial chemistry , asymmetric carbon , stereochemistry , organic chemistry , catalysis , mathematics , optically active , mathematical analysis , alkyl

The cupreidinium salt 1 catalyzes the highly enantioselective conjugate addition of nitromethane to β‐aryl‐β‐trifluoromethyl aryl enones ( 2 ). The biologically important chiral pyrrolines 4 and N‐oxide 5 , having a trifluoromethylated all‐carbon quaternary chiral center, were easily synthesized from the key intermediate ( R )‐ 3 in high to excellent yields. M.S.=molecular sieves.

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