Enantioselective reduction of nitroalkene mixtures by in situ equilibration

被引:25
作者
Czekelius, Constantin [1 ]
Carreira, Erick M. [1 ]
机构
[1] ETH Honggerberg, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
D O I
10.1021/op700029m
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We document an easy protocol for the enantioselective conjugate reduction of isomeric mixtures of nitroalkenes. Employing a catalyst from (CuOBu)-Bu-t and JOSIPHOS, conjugated and nonconjugated isomers are interconverted by the action of quaternary ammonium bases, and both reduced enantioselectively to the corresponding nitroalkanes.
引用
收藏
页码:633 / 636
页数:4
相关论文
共 27 条
[1]   Dramatic improvement of the enantiomeric excess in the asymmetric conjugate addition reaction using new experimental conditions [J].
Alexakis, A ;
Benhaim, C ;
Rosse, S ;
Humam, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (19) :5262-5263
[2]  
Berner OM, 2002, EUR J ORG CHEM, V2002, P1877
[3]   Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to nitroalkenes [J].
Choi, H ;
Hua, ZH ;
Ojima, I .
ORGANIC LETTERS, 2004, 6 (16) :2689-2691
[4]   Application of the chiral bis(phosphine) monoxide ligand to catalytic enantioselective addition of dialkylzinc reagents to β-nitroalkenes [J].
Cote, Alexandre ;
Lindsay, Vincent N. G. ;
Charette, Andre B. .
ORGANIC LETTERS, 2007, 9 (01) :85-87
[5]   Convenient transformation of optically active nitroalkanes into chiral aldoximes and nitriles [J].
Czekelius, C ;
Carreira, EM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (04) :612-615
[6]   Catalytic enantioselective conjugate reduction of β,β-disubstituted nitroalkenes [J].
Czekelius, C ;
Carreira, EM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (39) :4793-4795
[7]  
Czekelius C., 2005, ANGEW CHEM, V117, P618
[8]   Highly enantioselective conjugate addition of dialkylzinc reagents to acyclic nitroalkenes:: A catalytic route to β2-amino acids, aldehydes, and alcohols [J].
Duursma, A ;
Minnaard, AJ ;
Feringa, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (13) :3700-3701
[9]   Ni(II)-bis[(R,R)-N,N′-dibenzylcyclohexane-1,2-diamine]Br2 catalyzed enantioselective Michael additions of 1,3-dicarbonyl compounds to conjugated nitroalkenes [J].
Evans, DA ;
Seidel, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9958-9959
[10]  
Feuer H., 1990, In Nitro Compounds: Recent Advances in Synthesis and Chemistry