Base-Catalyzed Highly Stereoselective Conversion of γ-Hydroxy-α,β-acetylenic Esters to γ-Acetoxy Dienoates

被引：11

作者：

Yue, Yang ^{[1
,2
]}

Yu, Xiao-Qi ^{[1
]}

Pu, Lin ^{[2
]}

机构：

[1] Sichuan Univ, Dept Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

[2] Univ Virginia, Dept Chem, Charlottesville, VA 22904 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 20期

基金：

美国国家科学基金会;

关键词：

alkyne addition; dienoates; hydroxyacetylenic esters; stereoselective synthesis; synthetic methods; PROPARGYLIC ALCOHOLS; REDOX ISOMERIZATION; ALDEHYDES; ALKYNYLATION; COMPLEX; MILD;

D O I：

10.1002/chem.200802355

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

gamma-Hydroxy-alpha,beta-acetylenic esters can be conveniently prepared from the reaction of methyl propiolate with aldehydes in the presence of ZnEt2 and N-methylimidazole at room temperature. It is discovered that the gamma-hydroxy-alpha,beta-acetylenic esters can be catalyzed by p-N,N-dimethylaminopyridine (DMAP) in acetic anhydride to generate the gamma-acetoxy dienoates with high stereo control. The mechanism of this conversion is investigated by NMR ananlyses and isotope labeling experiments. An intramolecular Diels-Alder reaction of a gamma-acetoxy dienoate is conducted to show the synthetic potential of these compounds.

引用

页码：5104 / 5107

页数：4

共 22 条

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