Asymmetric synthesis of O-benzoyl cyanohydrins by reaction of aldehydes with benzoyl cyanide catalysed by BINOLAM-Ti(IV) complexes

被引：48

作者：

Baeza, A

Nájera, C

Sansano, JM

Saá, JM

机构：

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

[2] Univ Alicante, Inst Sintesis Organ, E-03080 Alicante, Spain

[3] Univ Illes Balears, Dept Quim, E-07071 Palma de Mallorca, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 14期

关键词：

D O I：

10.1016/j.tetasy.2005.05.031

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric cyanobenzoylation of aldehydes has been carried out for the first time, by reaction with benzoyl cyanide in a process catalysed by either (R)- or (S)-3,3'-bis(diethylaminomethyl)-1,1'-binaphthol BINOLAM-Ti(IV) complexes at room temperature and without additives. The reaction can be described as an overall cyano-O-benzoylation of aldehydes where a Lewis acid-Bronsted base (LABB) dual role for the catalyst induced firstly the key enantioselective hydrocyanation, which is then followed by O-benzoylation furnishing enantioenriched O-benzoyl cyanohydrins. (C) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2385 / 2389

页数：5

共 49 条

[41] Enzymatic C-C bond-forming reactions in organic synthesis [J].