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Synthesis 2011(21): 3453-3462  
DOI: 10.1055/s-0030-1260210
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Polyfunctional Tetrasubstituted Alkenyl Sulfides via a Carbocupration of Alkynyl Sulfides with Aryl and Benzylic Diorganozincs

Cora Dunsta, Albrecht Metzgera, Elena A. Zaburdaevaa,b, Paul Knochel*a
a Ludwig-Maximilians-Universität München, Department Chemie, Butenandtstr. 5-13, Haus F, 81377 München, Germany
Fax: +49(89)218077680; e-Mail: paul.knochel@cup.uni-muenchen.de;
b Lobachevsky State University of Nizhni Novgorod, Chemistry Department, 23 Prospekt Gagarina, 603950, Nizhni Novgorod, Russian Federation
Fax: +7(831)4623085; e-Mail: zaea4@rambler.ru;
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Publication History

Received 29 July 2011
Publication Date:
07 September 2011 (online)

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Abstract

A general method for the synthesis of tetrasubstituted alkenyl sulfides has been developed by the carbocupration of alkyn­yl sulfides with functionalized diorganozinc reagents in the presence of CuCN˙2LiCl. The intermediate alkenylcopper reagents readily react with various electrophiles furnishing a broad range of highly functionalized alkenes with excellent stereoselectivity (E/Z 93:7-99:1).

Key words

alkynyl sulfides - copper - zinc - carbometalation - olefins

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