Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process

A highly efficient two-step regio and stereoselective method for the synthesis of both cis-vinyltrimethylstannanes and cis-vinylpinacolboronates is described. This method takes advantage of the known lithium/tellurium exchange pathway providing a versatile alternative to known literature methods. The methodology presented demonstrates compatibility, for example, with substrates bearing oxygen functionality in comparison to previously reported methods of cis-selective hydrostannylation (i.e., ZrCl4).