Selective O-acylation of silyl enol ethers with acid halides mediated by a copper(I) salt

被引：15

作者：

Ito, H ^{[1
]}

Ishizuka, T ^{[1
]}

Tateiwa, J ^{[1
]}

Hosomi, A ^{[1
]}

机构：

[1] Univ Tsukuba, Dept Chem, Tsukuba, Ibaraki 3058571, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 35期

关键词：

silicon and compounds; copper and compounds; enolates; esterification;

D O I：

10.1016/S0040-4039(98)01334-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new selective synthetic method of enol esters (O-acylated products) from silyl enol ether and acid chloride in the presence of CuCl is described. This reaction proceeds smoothly in DMI (1,3-dimethyl-2-imidazolidinone) but not in a less polar solvent. The silicon-copper exchange reaction pathway is proposed for this transformation as in the cases of hydrosilane and alkynylsilane which were previously reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6295 / 6298

页数：4

共 30 条

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[26] Dichloro[TADDOLato(2-)-O,O′]titanium/dichlorobis[1-methylethoxy]titanium-mediated, highly diastereo- and enantioselective additions of silyl enol ethers to nitro olefins and [3+2] cycloadditions of primary adducts to acetylenes
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[27] Copper(I) tert-butoxide-promoted 1,4 Csp2-to-O silyl migration:: Generation of vinyl copper equivalents and their stereospecific cross-coupling with allylic, aryl, and vinylic halides
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[28] Copper(I) salt catalyzed reaction of 1,1,1-trichloro-2,2,2-trifluoroethane with trimethylsilyl enol ethers. A convenient synthesis of β3-chloro-β-(trifluoromethyl) α,β-unsaturated carbonyl compounds
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