One-pot synthesis of mixed (Z)-1,2-bis(organylchalcogene)-1-alkenes precursors of the novel β-organylthio vinyllithium intermediates

被引：5

作者：

Dabdoub, Miguel J. ^{[1
]}

Dabdoub, Vania B. ^{[1
]}

Pereira, Marco A. ^{[1
]}

Baroni, Adriano C. M. ^{[2
]}

Marques, Francisco A. ^{[3
]}

de Oliveira, Paulo R. ^{[4
]}

Guerrero, Palimecio G., Jr. ^{[4
]}

机构：

[1] Univ Sao Paulo, Lab Compostos Organocalcogenios, Ribeirao Preto, SP, Brazil

[2] Univ Fed Mato Grosso do Sul, UFMS, Dept Farm Bioquim, Campo Grande, MS, Brazil

[3] Univ Fed Parana, UFPR, Dept Quim, BR-80060000 Curitiba, Parana, Brazil

[4] Univ Tecnol Fed Parana, UTFPR, Lab Sintese Organ & Produtos Nat, Dept Quim & Biol, Curitiba, Parana, Brazil

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 39期

关键词：

Hydrochalcogenation; Transmetallation; Thioacetylenes; beta-Organylthio vinyllithium; STEREOSELECTIVE-SYNTHESIS; VINYLIC TELLURIDES; REGIOSELECTIVE-SYNTHESIS; VERSATILE GENERATION; TE/LI EXCHANGE; HIGHLY REGIO; HYDROZIRCONATION; HYDROALUMINATION; SELENIDES; SULFIDES;

D O I：

10.1016/j.tetlet.2010.07.112

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot hydrochalcogenation of 1-phenylthioacetylenes using organylselenolate and organyltellurolate anions generated by the insertions of selenium and tellurium in n-organyl lithium produced (Z)-1,2-bis(organylchalcogene)-1-alkenes. The chemical reactivity of these mixed 1,2-bis(organylchalcogene)-1-alkenes was studied by Te/Li and Se/Li stereoretentive exchanges carried out with n-butyl lithium, furnishing the new intermediate species (Z)-beta-organylthio vinyllithium anions, which were trapped with aldehydes, to give the (Z)-3-hydroxy vinyl thioethers with total control of the regio- and stereochemistry. (c) 2010 Elsevier Ltd. All rights reserved.

引用

页码：5141 / 5145

页数：5

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