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.
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收藏
页码：428 / 430
页数：3
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