手性二氧杂环丙烷对α,β-不饱和酯的高度对映选择性环氧化反应。

Highly enantioselective epoxidation of alpha, beta-unsaturated esters by chiral dioxirane.

作者信息

Wu Xin-Yan, She Xuegong, Shi Yian

机构信息

Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.

出版信息

J Am Chem Soc. 2002 Jul 31;124(30):8792-3. doi: 10.1021/ja020478y.

DOI:10.1021/ja020478y

PMID:12137521

Abstract

This paper describes a highly enantioselective epoxidation of alpha,beta-unsaturated esters using the fructose-derived ketone 2 as catalyst and Oxone as oxidant. High ee's have been obtained for a number of trans and trisubstituted substrates (82-98% ee). The results described show that it is feasible for dioxiranes to effectively epoxidize electron-deficient olefins with high ee's.

摘要

本文描述了使用果糖衍生的酮2作为催化剂、过一硫酸氢钾复合盐作为氧化剂，对α,β-不饱和酯进行高度对映选择性环氧化反应。对于多种反式和三取代底物，已获得了高对映体过量值（ee值为82%-98%）。所描述的结果表明，二氧杂环丙烷以高ee值有效环氧化缺电子烯烃是可行的。