Preparation of enol ester epoxides and their ring-opening to α-silyloxyaldehydes

被引：5

作者：

Friestad, Gregory K. ^{[1
]}

Sreenilayam, Gopeekrishnan ^{[1
]}

Cannistra, Joseph C. ^{[1
]}

Slominski, Luke M. ^{[1
]}

机构：

[1] Univ Iowa, Dept Chem, Iowa City, IA 52242 USA

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 38期

基金：

美国国家科学基金会;

关键词：

Enol esters; Epoxides; Aldehydes; Oxidation; SILICON TETHER APPROACH; THIYL RADICAL-ADDITION; ASYMMETRIC DIHYDROXYLATION; CHIRAL HYDRAZONES; ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; HYDROXY ALDEHYDES; KETONES; OXIDATION; 1,2-DIOLS;

D O I：

10.1016/j.tetlet.2012.06.142

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Z-selective ruthenium-catalyzed addition of aromatic carboxylic acids to alkynes was followed by dioxirane epoxidation to furnish enol ester epoxides with cis configuration. Upon treatment of enol ester epoxides with tert-butyldimethylsilyl triflate in the presence of 2,6-lutidine, synthetically useful alpha-silyloxyaldehydes were obtained. This novel transformation was facilitated by microwave irradiation. (C) 2012 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5064 / 5067

页数：4

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