ASYMMETRIC-SYNTHESIS OF LPHA-SUBSTITUTED)-HYDROXYMETHYL[2.2]PARACYCLOPHANE AND LPHA-SUBSTITUTED)-HYDROXYMETHYL[2.2]PARACYCLOPHANE AND DERIVATIVES BY STEREOSELECTIVE ADDITION TO (R)-4-HYDROXY-5-FORMYL[2.2]PARACYCLOPHANE AND DERIVATIVES

Highly diastereoselective nucleophilic addition reactions of organomet allic reagents to formyl[2.2]paracyclophane derivatives which were ort ho-substituted by hydroxy-, alkoxy- and trimethylsilyloxy-groups are r eported. The absolute configuration of the newly formed secondary alco hols is assigned on the basis of the X-ray diffraction study as well a s chemical correlation. The magnitude of the asymmetric induction and even the sense of chirality of the forming asymmetric carbon atoms of the alcohols depended on the nature of the ortho-substituents. Copyrig ht (C) 1996 Elsevier Science Ltd