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

被引：101

作者：

Kawai, Hiroyuki ^{[1
]}

Yuan, Zhe ^{[1
]}

Kitayama, Takashi ^{[1
]}

Tokunaga, Etsuko ^{[1
]}

Shibata, Norio ^{[1
]}

机构：

[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 21期

基金：

日本科学技术振兴机构;

关键词：

enantioselectivity; fluorine; heterocycles; organocatalysis; synthetic methods; ASYMMETRIC MICHAEL ADDITION; QUATERNARY AMMONIUM-SALT; NITROALKANES; CHALCONES; ORGANOCATALYST; ALKYLATION; CATALYSIS;

D O I：

10.1002/anie.201301123

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5575 / 5579

页数：5

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