Enantioselective addition of dimethylzinc to aldehydes:: assessment of optimal N,N-substitution for 2-dialkylamino-1,1,2-triphenylethanol ligands

被引:51
作者
García-Delgado, N
Fontes, M
Pericàs, MA
Riera, A
Verdaguer, X
机构
[1] Univ Barcelona, URSA PCB, Unitat Recerca Sintesi Asimetr, E-08028 Barcelona, Spain
[2] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain
关键词
D O I
10.1016/j.tetasy.2004.05.026
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A general methodology for the synthesis of 2-dialkylamino-1,1,2-triphenylethanol has been developed. Novel ligands 3, 4, and 5, bearing flexible alkyl chains on nitrogen have been synthesized by epoxide-ring opening of the encumbered (S)-triphenyloxirane. These ligands along with 2-piperidino-1,1,2-triphenyl ethanol 1 have been tested in the addition of dimethylzinc to aldehydes. This allowed for the assessment of the structural features that favor the catalytic activity and selectivity of the ligands with respect to nitrogen substitution. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2085 / 2090
页数:6
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