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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.