Generation and Applications of α-Chiral Allylic Stannanes

Significance

Previously, the authors have reported the copper-catalyzed reaction of soft bis(triorganosilyl) zinc reagents for carbon-silicon bond formation. In the present paper the authors apply this methodology to the use of bis(triorganostannyl) zinc reagents in the enantiospecific synthesis of all-carbon-substituted allylic stannanes. These stannanes could subsequently undergo either thermal or Lewis acid promoted S_E2′ reactions with aldehydes to give anti- or syn-homoallylic alcohols in high diastereoselectivities with nearly complete chirality transfer.