Enantioselective addition of diethylzinc to aldehydes catalyzed by D-glucosamine derivatives: Highly pronounced effect of trifluoromethylsulfonamide

被引：16

作者：

Bauer, Tomasz ^{[1
]}

Smolinski, Slawomir ^{[1
]}

机构：

[1] Warsaw Univ, Dept Chem, PL-02093 Warsaw, Poland

来源：

APPLIED CATALYSIS A-GENERAL | 2010年 / 375卷 / 02期

关键词：

D-Glucosamine; Diethylzinc; Titanium tetraisopropoxide; Enantioselective; Trifluoromethylsulfonamide; ASYMMETRIC ADDITION; TITANIUM; DIALKYLZINC; COMPLEXES; ALKYLATION; MECHANISM; REAGENTS;

D O I：

10.1016/j.apcata.2010.01.009

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We present the synthesis of beta-hydroxy sulfonamides derived from D-glucosamine and their application as ligands in titanium tetraisopropoxide promoted enantioselective addition of diethylzinc to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-trifluoromethylosulfonamido-D-glucosamine derivative is one of the most active ligands known and only 1 mol% of the ligand is sufficient for efficient catalysis of diethylzinc addition. The reaction is highly enantioselective for some aromatic aldehydes and enantiomeric excess up to 99% was obtained. (C) 2010 Elsevier B.V. All rights reserved.

引用

页码：247 / 251

页数：5

共 23 条

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