Organylzinc Chalcogenolate Promoted Michael-Type Addition of α,β-Unsaturated Carbonyl Compounds

被引：16

作者：

Nunes, Vanessa Loren ^{[1
]}

de Oliveira, Ingryd Cristina ^{[1
]}

do Rego Barros, Olga Soares ^{[1
]}

机构：

[1] Univ Fed Goias, Inst Quim, BR-74001970 Goiania, Go, Brazil

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 07期

关键词：

Michael addition; Zinc; Chemoselectivity; Regioselectivity; ORGANOSELENIUM CHEMISTRY; THIOLS; ZINC; CYCLIZATION; SELENIDES; HALIDES; BOND;

D O I：

10.1002/ejoc.201301497

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present the chemo-, regio-, and stereoselective synthesis of vinyl chalcogenide compounds promoted by organylzinc chalcogenolates. In this protocol, reductive cleavage of diorganyl dichalcogenide bonds by the Zn/NH4OH system led to organylzinc chalcogenolates. The reaction was performed with propiolic acids and esters and afforded -organochalcogenacrylic acids and esters under mild basic conditions. The stereochemistry corresponded to anti-Markovnikov addition of the organyl chalcogenolate constituents across the triple bond.

引用

页码：1525 / 1530

页数：6

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