Vinyl triflates derived from 1,3-dicarbonyl compounds and analogs: access and applications to organic synthesis

被引：52

作者：

Chassaing, Stefan ^{[2
,3
]}

Specklin, Simon ^{[1
]}

Weibel, Jean-Marc ^{[1
]}

Pale, Patrick ^{[1
]}

机构：

[1] Univ Strasbourg, Inst Chim Strasbourg, Lab Synth & Reactivite Organ, F-67000 Strasbourg, France

[2] Univ Toulouse, ITAV UMS 3039, F-31106 Toulouse, France

[3] Univ Toulouse 3, CNRS, UMR 5068, Lab Synth & Physicochim Mol Interet Biol, F-31062 Toulouse 9, France

来源：

TETRAHEDRON | 2012年 / 68卷 / 36期

关键词：

Triflate; Vinyl triflate; 1,3-Dicarbonyl; Synthesis; CROSS-COUPLING REACTION; ENOL ELIMINATION-REACTIONS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; DECARBOXYLATIVE ELIMINATION; CONVENIENT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; CATALYZED ALKENYLATION; ASYMMETRIC-SYNTHESIS;

D O I：

10.1016/j.tet.2012.05.107

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

This review details the current methods used to prepare vinyl triflates derived from 1,3-dicarbonyl compounds and describes the reactivity of such functionalized vinyl triflates. alpha-Ketovinyl triflates can easily and stereoselectively be produced through three different ways. Enolization and triflation is the most common route, but direct triflation with triflic anhydride could also be used, each involving different mechanisms. Direct addition of triflic acid and related sulfonic acids to triple bond offers an alternative to the previous methods. With their peculiar set of functional groups, alpha-ketovinyl triflates can react in four different ways. The vinyl triflate part could be engaged in coupling reactions, while the carbonyl group as well as the enone motif could be subjected to nucleophilic additions. If a proton is available next to the triflate group, eliminations could occur under basic conditions. Upon addition, fragmentations could also be possible. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：7245 / 7273

页数：29

共 176 条

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