Asymmetric Construction of (E)-δ-Stannyl Homoallylic Alcohols

Significance

The hydroboration of aldehydes with allylborane reagents usually gives homoallylic alcohols with terminal vinyl and β-substituents. In this work, the authors envisioned the β-carbocation-stabilizing effect of trialkyltin and succeeded the synthesis of (E)-δ-stannyl homoallylic alcohols in high stereoselectivities. These compounds could be very useful chiral synthetic building blocks upon further functionalization.