We recently discovered that alpha-chloroalkylorganomagnesium and alpha-chloroalkyllithium reagents, generated in highly enantioenriched form (%ee > 98%) by sulfoxide ligand exchange, insert into the carbon-boron bond of boronic esters with remarkable stereochemical fidelity. Successful iteration of this type of stereospecific carbon-carbon bond forming process would provide a powerful and fully programmable approach for acyclic stereocontrol not based upon the usual precepts of stereoinduction. Our on going attempts to realize the iterative stereospecific reagent controlled homologation of boronates will be presented along with allied efforts directed at optimizing the complex sulfoxide ligand exchange phenomena used to generate the carbenoid reagents of interest.