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
收藏
页码：5104 / 5107
页数：4
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