Calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids

被引：64

作者：

Bozkurt, Selahattin ^{[1
]}

Durmaz, Mustafa ^{[1
]}

Yilmaz, Mustafa ^{[1
]}

Sirit, Abdulkadir ^{[1
]}

机构：

[1] Selcuk Univ, Dept Chem, TR-42099 Konya, Turkey

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 05期

关键词：

D O I：

10.1016/j.tetasy.2008.02.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of the first calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids has been achieved in two steps from p-tert-butylcalix[4]arene. The catalytic efficiency of the chiral calix[4]arenes 3a-c was evaluated by carrying out the phase-transfer alkylation of N-(diphenylmethylene)glycine ethyl ester with benzyl bromide. Various factors that affect the chemical yield and enantio selectivity were also examined. Benzylation of glycine imine 4 using calix[4]arene- based dimeric catalyst 3a as a chiral phase-transfer catalyst in toluene/CHCl3 mixture (7:3 v/v) at 0 degrees C gave the best enantioselectivities and yields in the presence of aqueous NaOH. (C) 2008 Elsevier Ltd. All rights reserved.

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页码：618 / 623

页数：6

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