A new approach to enantioselective cyanation of imines with Et2AlCN

被引:117
作者
Nakamura, S [1 ]
Sato, N [1 ]
Sugimoto, M [1 ]
Toru, T [1 ]
机构
[1] Nagoya Inst Technol, Grad Sch Engn, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
D O I
10.1016/j.tetasy.2004.03.040
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An enantioselective Strecker-type reaction of imines with Et2AlCN in the presence of chiral additives has been examined. The enantioselectivity varied depending on the substituents of the imino group as well as the chiral additives used. Thus, alpha-aminonitriles were obtained in good yields with good en antioselectivities in the reaction of N-benzylidenebenzhydrylamine with Et2AlCN and BINOL. The reaction with excess BINOL gave the aminonitrile with reversed configuration. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码:1513 / 1516
页数:4
相关论文
共 57 条
[51]   Reversal of stereochemistry in enantioselective transformations. Can they be planned or are they just accidental? [J].
Sibi, MP ;
Liu, M .
CURRENT ORGANIC CHEMISTRY, 2001, 5 (07) :719-755
[53]  
Takamura M, 2000, ANGEW CHEM INT EDIT, V39, P1650, DOI 10.1002/(SICI)1521-3773(20000502)39:9<1650::AID-ANIE1650>3.0.CO
[54]  
2-P
[55]   Structure-based analysis and optimization of a highly enantioselective catalyst for the Strecker reaction [J].
Vachal, P ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (34) :10012-10014
[56]  
Yet L, 2001, ANGEW CHEM INT EDIT, V40, P875, DOI 10.1002/1521-3773(20010302)40:5<875::AID-ANIE875>3.0.CO
[57]  
2-C