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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 20
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Original Articles

A Simple and Stereoselective Synthesis of E-Vinylstannanes via Diisobutylalane Reduction of Alkynes

Brian L. Groh University of Minnesota-Duluth, Duluth, Minnesota, 55812-2496
,
Arlette F. Kreager University of Minnesota-Duluth, Duluth, Minnesota, 55812-2496
&
Janie B. Schneider University of Minnesota-Duluth, Duluth, Minnesota, 55812-2496
Pages 2065-2076 | Received 30 May 1991, Published online: 23 Sep 2006
 
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Abstract

A simple, one-pot method has been developed for the preparation of E-vinylstannanes from alkynes with high stereo- and regioselectivity to afford vinylstannanes in good yield. This is accomplished by successive treatment of an alkyne with DIBAL, an alkyllithium reagent, and a tin electrophile.

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