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

页码：777 / 780

页数：4

共 18 条

[1] Addition of dialkylzinc to ketones in the presence of silylating agents: Synthesis of functionalized tertiary silyl ethers [J].