Identification of new catalysts for the asymmetric reduction of imines into chiral amines with polymethylhydrosiloxane using high-throughput screening

被引:27
作者
Ireland, T [1 ]
Fontanet, F [1 ]
Tchao, GG [1 ]
机构
[1] Rhodia, Lyon Res Ctr, Catalysis Dept, F-69192 St Fons, France
关键词
asymmetric imine reduction; PMHS; high-throughput screening;
D O I
10.1016/j.tetlet.2004.03.159
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The use of high-throughput techniques allowed the rapid identification of new catalysts for the enantioselective reduction of imines using polymethylhydrosiloxane (PMHS) as a reducing agent. By a simple modification of the chiral ligand structure that came out of the screening, the enantioselectivity of the reduction was increased from 40% ee to 60% ec. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4383 / 4387
页数:5
相关论文
共 26 条
[1]   Direct Zn-diamine promoted reduction of C=O and C=N bonds by polymethylhydrosiloxane in methanol [J].
Bette, V ;
Mortreux, A ;
Lehmann, CW ;
Carpentier, JF .
CHEMICAL COMMUNICATIONS, 2003, (03) :332-333
[2]  
Chandrasekhar S, 2000, SYNLETT, P1655
[3]   Inexpensive protocol for reduction of imines to amines using polymethylhydrosiloxane (PMHS) [J].
Chandrasekhar, S ;
Reddy, MV ;
Chandraiah, L .
SYNTHETIC COMMUNICATIONS, 1999, 29 (22) :3981-3987
[4]  
Courmarcel J, 2001, ISR J CHEM, V41, P231
[5]   Catalytic enantioselective conjugate reduction of β,β-disubstituted nitroalkenes [J].
Czekelius, C ;
Carreira, EM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (39) :4793-4795
[6]   A method for the asymmetric hydrosilylation of N-aryl imines [J].
Hansen, MC ;
Buchwald, SL .
ORGANIC LETTERS, 2000, 2 (05) :713-715
[7]   Oxazaborolidine mediated asymmetric ketone reduction: prediction of enantiomeric excess based on catalyst structure [J].
Hoogenraad, M ;
Klaus, GM ;
Elders, N ;
Hooijschuur, SM ;
McKay, B ;
Smith, AA ;
Damen, EWP .
TETRAHEDRON-ASYMMETRY, 2004, 15 (03) :519-523
[8]  
Jandeleit B, 1999, ANGEW CHEM INT EDIT, V38, P2495
[9]   Catalytic enantioselective addition to imines [J].
Kobayashi, S ;
Ishitani, H .
CHEMICAL REVIEWS, 1999, 99 (05) :1069-1094
[10]   Polymethylhydrosiloxane: a versatile reducing agent for organic synthesis [J].
Lawrence, NJ ;
Drew, MD ;
Bushell, SM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (23) :3381-3391