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
收藏
页码：2703 / 2709
页数：7
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