Ruthenium-catalysed asymmetric transfer hydrogenation of N-(tert-butanesulfinyl)imines

被引：46

作者：

Guijarro, David ^{[1
]}

Pablo, Oscar

Yus, Miguel

机构：

[1] Univ Alicante, Fac Ciencias, Dept Quim Organ, Alicante 03080, Spain

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 38期

关键词：

Sulfinylimine; Diastereoselective reduction; Asymmetric transfer hydrogenation; Ruthenium catalyst; Chiral primary amine; TERT-BUTANESULFINYL IMINES; ENANTIOSELECTIVE ADDITION; DIALKYLZINC REAGENTS; DIASTEREOSELECTIVE ADDITION; BETA-AMINOALCOHOLS; PROLINOL SKELETON; CHIRAL AZIRIDINES; AMINES; REDUCTION; N-(DIPHENYLPHOSPHINOYL)IMINES;

D O I：

10.1016/j.tetlet.2009.07.044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ruthenium complex prepared from [RuCl(2)(p-cymene)](2) and (1S,2R)-1-amino-2-indanol is a very efficient catalyst for the asymmetric transfer hydrogenation of (R)-N-(tert-butanesulfinyl)ketimines in iso-propanol. By carefully removing all possible moisture from the reaction medium, chiral primary amines with very high optical purities (up to >99% ee) can be easily prepared in excellent yields by the diastereoselective reduction of the imines followed by removal of the sulfinyl group under mild acidic conditions. Reaction times of 1-4 h were needed to complete the reduction reactions when they were performed at 40 degrees C. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：5386 / 5388

页数：3

共 37 条

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