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

共 64 条

[1]

Akagawa K., 2012, ANGEW CHEM, V124, P12958

[2] Synthesis and applications of C2-symmetric guanidine bases [J].

Allingham, MT ;

Howard-Jones, A ;

Murphy, PJ ;

Thomas, DA ;

Caulkett, PWR .

TETRAHEDRON LETTERS, 2003, 44 (48) :8677-8680

[3]

[Anonymous], 2010, ANGEW CHEM

[4]

[Anonymous], 2011, ANGEW CHEM INT ED, V50, P10565

[5]

[Anonymous], 2009, ANGEW CHEM INT ED, V48, p3224 3242

[6]

[Anonymous], 2010, ANGEW CHEM INT ED, V49, P5762

[7]

[Anonymous], 2006, ANGEW CHEM INT ED, V45, P7496

[8]

[Anonymous], 2006, ANGEW CHEM

[9]

[Anonymous], 2012, ANGEW CHEM INT ED, V51, P4959

[10]

[Anonymous], 2006, ANGEW CHEM INT ED, V45, P1520

← 1 2 3 4 5 6 7 →