Synthesis of 7-Oxabicyclo[2.2.1]heptanes and 8-Oxabicyclo[3.2.1]octanes from C-Glycosides via an Intramolecular Cyclization

被引：1

作者：

Zou, Wei ^{[1
]}

Vembaiyan, Kannan ^{[1
]}

机构：

[1] Natl Res Council Canada, Inst Biol Sci, Ottawa, ON K1A 0R6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期

关键词：

CATALYZED 4+3 CYCLOADDITION; ASYMMETRIC-SYNTHESIS; FORMAL SYNTHESIS; CARBONYL YLIDES; DERIVATIVES; FURAN; CATIONS; INHIBITOR; SUGARS;

D O I：

10.1021/jo3024973

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and effective method for the synthesis of 7-oxabicyclo[2.2.1]heptanes and 8-oxabicyclo[3.2.1]octanes from acetonyl C-glycoside substrates is described, which involves an intramolecular cyclization reaction through a nucleophilic substitution at C-5 or C-6 of C-glycosides by a 2'-enamine intermediate formed in the presence of pyrrolidine. Because anomeric epimerization occurs under these conditions, C-glycoside substrates with either anomeric configuration were converted to the same product(s) in same stereoselectivity and similar chemical yield.

引用

页码：2703 / 2709

页数：7

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