POLYMER ATTACHED CYCLIC DIPEPTIDES AS CATALYSTS FOR ENANTIOSELECTIVE CYANOHYDRIN FORMATION

被引：26

作者：

KIM, HJ ^{[1
]}

JACKSON, WR ^{[1
]}

机构：

[1] MONASH UNIV,DEPT CHEM,CLAYTON,VIC 3168,AUSTRALIA

来源：

TETRAHEDRON-ASYMMETRY | 1992年 / 3卷 / 11期

基金：

澳大利亚研究理事会;

关键词：

D O I：

10.1016/0957-4166(92)80019-S

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Derivatives of cyclo-[(S)-Tyr-(S)-His], related to the 'Inoue' catalyst, cyclo-[(S)-Phe-(S)-His] have been attached to chloromethylated polystyrene and to polysiloxane polymers via spacer groups coupled to the tyrosine phenolic residue. These polymer-attached dipeptides have been shown to be efficient catalysts for the conversion of aromatic aldehydes to cyanohydrins but enantioselectivities are low. The loss of enantioselectivity relative to the Inoue catalyst has been attributed to steric effects from the substituents on the tyrosyl phenolic group. Some mechanistic comments regarding the preferred conformation of the active dipeptide are made.

引用

页码：1421 / 1430

页数：10

共 15 条

[1] NMR MEASUREMENTS AND SEMIEMPIRICAL CALCULATIONS IN A 1ST APPROACH TO ELUCIDATE THE MECHANISM OF ENANTIOSELECTIVE CYANOHYDRIN FORMATION CATALYZED BY CYCLO-(S)-PHE-(S)-HIS [J].