Stereoselective Synthesis and Functionalization of Acetylenic Boronic Esters

Abstract

Hydrozirconation of homopropargyl boronic esters, readily available by Matteson homologation, allows their selective functionalization while preserving the boronic ester functionality. Metal–halogen exchange yields reactive vinyl iodides, which can be further converted into functionalized alkenes via Negishi couplings and Heck reactions. These reactions are used to generate polyketide-like structures, which are relevant for the synthesis of natural products.