Silver-Assisted, Iridium-Catalyzed Allylation of Bis[(pinacolato)boryl]methane Allows the Synthesis of Enantioenriched Homoallylic Organoboronic Esters

Described here is
an enantioselective approach of making chiral,
β-substituted homoallylic organoboronic esters. In the presence
of LiOtBu and a catalytic amount of silver
salt, commercial bis­[(pinacolato)­boryl]­methane participated in the
iridium-catalyzed asymmetric allylation reactions, delivered a “CH2B­(pin)” group, and yielded the title compounds from
allylic carbonates. The synthetic utility of the prepared chiral organoboronates
was demonstrated by their conversion to other important classes of
compounds.