Stereoselective synthesis of homoallylic alcohols of the [2,2]paracyclophane series and their use as auxiliaries in asymmetric allylboration of aldehydes

Stereoselectivity of allylboration of 4-formyl[2.2]paracyclophane, 4-acetyl [2.2]paracyclophane, and 4-hydroxy-5-formyl[2.2]paracyclophane was studied and the relative configurations of the homoallylic alcohols obtained were e stablished. Optically pure (Sp.Sc)-(+)-4-(1-hydroxy-1-methylbut-3-enyl)[2.2 ]paracyclophane and (Rc,Sc)-(+)-4-hydroxy-5-(1-hydroxybut-3-enyl)[2.2]parac yclophane were synthesized. The possibility of using (Sp,Sc)-(+)-4-(1-hydro xy-1-methylbut-3-enyl)[2.2]paracyclophane as a recoverable chiral auxiliary in asymmetric allylboration of aldehydes was demonstrated.