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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