General Stereospecific Synthesis of Trisubstituted Alkenes via Stepwise Hydroboration

Abstract

Iodination of alkenylalkylbromoboranes, obtained via the hydroboration of internal alkynes with alkylbromoboranes, in the presence of sodium methoxide in methanol, results in the formation of trisubstituted alkenes of established stereochemistry, thus providing a general synthesis of trisubstituted alkenes with unambiguous stereochemistry. © 1982, American Chemical Society. All rights reserved.