Synthesis of novel Schiff base ligands from gluco- and galactochloraloses for the Cu(II) catalyzed asymmetric Henry reaction

被引：13

作者：

Alkan, Sevda ^{[1
]}

Telli, Fatma C. ^{[1
]}

Salman, Yesim ^{[1
]}

Astley, Stephen T. ^{[1
]}

机构：

[1] Ege Univ, Fac Sci, Dept Chem, TR-35100 Izmir, Turkey

来源：

CARBOHYDRATE RESEARCH | 2015年 / 407卷

关键词：

Chloralose; Asymmetric Henry reaction; Chiral Schiff base; Amino sugar; PROMOTED INTRAMOLECULAR FORMATION; WITTIG-CYCLIZATION PROCEDURE; NITROALDOL REACTION; ALPHA-KETOESTERS; SUGARS; DERIVATIVES; CHLORALOSE; ACETALS;

D O I：

10.1016/j.carres.2015.01.023

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of chiral Schiff base ligands has been prepared using aminochloralose derivatives of glucose and galactose. These ligands were used as catalysts in the asymmetric Henry reaction in the presence of Cu(II) ions giving yields of up to 95%. An interesting solvent dependency on enantiomeric control was observed with the best enantiomeric excesses (up to 91%) being obtained in the presence of water. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：97 / 103

页数：7

共 55 条

[1] (R)-3,4,5-trideoxy-5,6-didehydro-1,2-O-(2,2,2-trichloroethylidene)-α-D-glucofuranose-6,3-carbolactone:: a new derivative of a α-chloralose [J].