Organylzinc Chalcogenolate Promoted Michael-Type Addition of [alpha],[beta]-Unsaturated Carbonyl Compounds

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 prop...

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Bibliographic Details
Published in:European journal of organic chemistry 2014-03, Vol.2014 (7), p.1525
Main Authors: Loren Nunes, Vanessa, de Oliveira, Ingryd Cristina, Soares do Rego Barros, Olga
Format: Article
Language:English
Subjects:
Beta
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Summary: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 [beta]-organochalcogenacrylic acids and esters under mild basic conditions. The stereochemistry corresponded to anti-Markovnikov addition of the organyl chalcogenolate constituents across the triple bond. [PUBLICATION ABSTRACT]
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201301497