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

Cora Dunst; Albrecht Metzger; Elena A. Zaburdaeva; Paul Knochel

doi:10.1055/s-0030-1260210

PAPER

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

Cora Dunst^a, Albrecht Metzger^a, Elena A. Zaburdaeva^a,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;

Abstract

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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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References

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