The dual-catalyzed (amino alcohol Lewis acid) enantioselective addition of diethylzinc to N-diphenylphosphinoyl imines

被引：40
|
作者：
Jimeno, C [1 ]
Vidal-Ferran, A [1 ]
Moyano, A [1 ]
Pericàs, MA [1 ]
Riera, A [1 ]
机构：
[1] Univ Barcelona, Dept Quim Organ, Unitat Reccerca Sintesi Aismetr, E-08028 Barcelona, Spain
来源：
TETRAHEDRON LETTERS | 1999年 / 40卷 / 04期
关键词：
imines; addition reactions; zinc and compounds; asymmetric induction;
D O I：
10.1016/S0040-4039(98)02410-1
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Optimal structural characteristics within a family of (2R,3R)-1-alkoxy-3-dialkylamino-3-phenyl-2-propanols have been determined for maximum enantioselectivity in the addition of diethylzinc to N-diphenylphosphinoyl imines (1-alkoxy = trityloxy; 3-dialkylamino = piperidino). The simultaneous use of silylating agents acting as Lewis acids to induce rate acceleration has been investigated, allowing the identification of triisopropylsilyl chloride and tert-butyldiphenylsilyl chloride as the most efficient mediators in terms of rate enhancement and enantiomeric excess of the resulting phosphinamides. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：777 / 780
页数：4
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