Gold(III) Chloride and Phenylacetylene: A Catalyst System for the Ferrier Rearrangement, and O-Glycosylation of 1-O-Acetyl Sugars as Glycosyl Donors

被引：35
作者：
Roy, Rashmi [1 ]
Rajasekaran, Parasuraman [1 ]
Mallick, Asadulla [1 ]
Vankar, Yashwant D. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 25期
关键词：
Synthetic methods; Homogeneous catalysis; Gold; Carbohydrates; Glycosylation; Rearrangement; STEREOSELECTIVE-SYNTHESIS; ORTHO-ALKYNYLBENZOATES; PENTENYL GLYCOSIDES; EFFICIENT PROCEDURE; ALPHA-GLUCOSIDES; FACILE SYNTHESIS; AMINO-ACIDS; PART; GLYCALS; SCOPE;
D O I：
10.1002/ejoc.201402606
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed a new catalyst system comprising AuCl3 and phenylacetylene that promotes the Ferrier rearrangement of glycals and 2-acetoxymethylglycals with different nucleophiles, and also the O-glycosylation of 1-O-acetyl sugars to obtain a variety of useful glycosides at room temperature through relay catalysis. Good anomeric selectivity was observed for the Ferrier rearrangements, whereas the Oglycosylation of 1-O-acetyl sugars gave mixtures of diastereomers with moderate to excellent selectivity.
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收藏
页码：5564 / 5573
页数：10
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