Stereoselective Synthesis and Functionalization of Acetylenic Boronic Esters

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.