ASYMMETRIC INDUCTION REACTIONS .6. ASYMMETRIC-SYNTHESIS OF A CYCLOPENTENE DERIVATIVE BY TRANSITION-METAL-CATALYZED ASYMMETRIC VINYLCYCLOPROPANE CYCLOPENTENE REARRANGEMENTS WITH CHIRAL PHOSPHINE-LIGANDS

Asymmetric synthesis of a cyclopentene derivative was accomplished by transition metal-catalyzed vinylcycloproane-cyclopentene rearrangement s with chiral phosphine ligands. A dramatic solvent effect was observe d on the nickel-catalyzed asymmetric rearrangement of a cyclopropane s ystem into an optically active cyclopentene derivative with chiral pho sphine ligands. The absolute configuration of the product was determin ed by chemical correlation to the compound of known absolute configura tion. The stereochemistry of the product was readily controlled by sel ecting the catalyst, nickel or palladium, with extremely high enantios electivity.