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-formyl2.2]paracyclophane, 4-acetyl2.2]paracyclophane, and 4-hydroxy-5-formyl2.2]paracyclophane was studied and the relative configurations of the homoallylic alcohols obtained were established. Optically pure (Sp,Sc)-(+)-4-(4-hydroxy-1-methylbut-3-enyl)2.2]paracyclophane and (Rc,Sc)-(+)-4-hydroxy-5-(4-hydroxybut-3-enyl)2.2]paracyclophane were synthesized. The possibility of using (Sp,Sc)-(+)-4-(4-hydroxy-4-methylbut-3-enyl)2.2]paracyclophane as a recoverable chiral auxiliary in asymmetric allylboration of aldehydes was demonstrated. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 914–921, May, 2000.