Silicon Fluorides for Acid-Base Catalysis in Glycosidations

被引：33

作者：

Kumar, Amit ^{[1
]}

Geng, Yiqun ^{[1
]}

Schmidt, Richard R. ^{[1
,2
]}

机构：

[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany

[2] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 08期

关键词：

arylsilicon fluorides; bifunctional catalysis; glycosidation; 1; 2-trans glycosides; O-glycosyl trichloroacetimidates; mechanism; EFFICIENT SYNTHESIS; BOND FORMATION; O-GLYCOSYL; DISACCHARIDES; REACTIVITY; CHEMISTRY; ENERGIES; HEATS; WEAK;

D O I：

10.1002/adsc.201100933

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Adduct formation between alcohols as glycosyl acceptors and phenylsilicon trifluoride (PhSiF3) as catalyst permits acid-base-atalyzed glycosidations with O-glycosyl trichloroacetimidates as glycosyl donors. In this way, from various glycosyl donors and acceptors 1,2-trans- and some 1,2-cis-glycosides could be obtained with high anomeric selectivity. A preference for an intramolecular bimolecular nucleophilic substitution (SN2-type) reaction course with concomitant donor and acceptor activation is supported by the results.

引用

页码：1489 / 1499

页数：11

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