Regio- and stereoselective preparation of (Z)-silyl enol ethers by three-component coupling using α,β-unsaturated acylsilanes as core building blocks

被引：16

作者：

Tsubouchi, Akira ^{[1
]}

Sasaki, Natsuki ^{[1
]}

Enatsu, Shouko ^{[1
]}

Takeda, Takeshi ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Koganei, Tokyo 1848588, Japan

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 10期

关键词：

Copper(I) tert-butoxide; Conjugate addition; Silyl enol ethers; Silyl migration; Three-component coupling; VINYL GRIGNARD-REAGENT; SILYL MIGRATION; CONJUGATE ADDITION; REGIOSELECTIVE SYNTHESIS; BROOK REARRANGEMENT; KETONES; GENERATION; CHEMISTRY; ALLYLATION; ALCOHOLS;

D O I：

10.1016/j.tetlet.2012.12.089

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on the conjugate addition-silyl migration-alkylation strategy, (Z)-silyl enol ethers possessing a stereocenter at the gamma-position were prepared with complete regio- and stereoselectivity by three-component coupling of alpha,beta-unsaturated acylsilanes, Grignard reagents (or cuprates)/copper(I) tert-butoxide, and organic halides. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1264 / 1267

页数：4

共 20 条

[1] Complete Regio- and Stereoselective Construction of Highly Substituted Silyl Enol Ethers by Three-Component Coupling
Tsubouchi, Akira
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (39) : 7089 - 7091
[2] Regio- and stereoselective synthesis of silyl enol ethers using a new base electrogenerated from hexamethyldisilazane
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Bordeau, M
Biran, C
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[3] Regio- and Stereoselective Synthesis of Silyl Enol Ethers Using a New Base Electrogenerated from Hexamethyldisilazane
J Org Chem, 16 (5532):
[4] Chemo-, regio- and stereoselective preparation of silyl enol ethers from thiol esters and bis(iodozincio)alkane
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[7] Stereospecific synthesis of tetrasubstituted Z-enol silyl ethers by a three component coupling process
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[10] Synthesis of cyclic silyl enol ethers from α-Aryl-α-diazoketones: new building blocks for preparation of indanones and α,β-unsaturated ketones
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