trans-Hydroalumination-Alkylation of Propargylic Alcohols

Significance

This is a simple method for the trans-hydroalumination-alkylation of propargylic alcohols, giving stereochemically defined trisubstituted allylic alcohols. This method complements the known procedure for the cis-hydroalumination-alkylation of allylic alcohols with DIBAL-H. The method uses inexpensive and relatively safe Vitride (Red-Al) as the hydroalumination agent. The method is not sensitive to the steric hindrance in the allylic alcohol. Only reactive electrophiles like allylic, benzylic and propargylic halides afford good yields of products.