ENANTIOSELECTIVE ADDITION OF DIETHYL ZINC TO BENZALDEHYDE CATALYZED BY TI(IV) AND GLUCOSE DERIVATIVES

被引：0

作者：

Parada, Jose ^{[1
]}

Mendoza, Jorge ^{[1
]}

Cisternas, Francy ^{[1
]}

Eguiluz, Angel ^{[1
]}

机构：

[1] Univ Chile, Fac Ciencias Quim & Farmaceut, Dept Quim Inorgan & Analit, Santiago, Chile

来源：

JOURNAL OF THE CHILEAN CHEMICAL SOCIETY | 2010年 / 55卷 / 04期

关键词：

diethylzinc; glucose derivatives; 1-phenyl-1-propanol; Ti(IV)-carbohydrate; AROMATIC-ALDEHYDES; COMPLEXES; ALCOHOLS; SUGAR;

D O I：

10.4067/S0717-97072010000400003

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

D-Glucose derivatives 1,2:5,6-di-O-isopropyline-a-D-glucofuranose (1) and 1,2-O-isopropyline-a-D-glucofuranose (2) with Ti(IV) are chiral catalysts in the addition of diethylzinc to benzaldehyde. The Ti(IV)-carbohydrate catalytic system is optimal with excess Ti(IV) and substoichiometric carbohydrate and 2 is the more active chiral catalyst probably because this derivative acts as a bidentate ligand in the proposed reaction. The arrangement of OH groups is crucial in determining the configuration of the alcohol product.

引用

页码：428 / 430

页数：3

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