A Novel Enantioselective Reaction. Palladium-catalyzed Enantiodistinctive Reaction of Bicyclic Allylic Compounds

Reaction of ((plus-minus))-2(beta)-acetoxy-4a(beta)-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalene (4) with dimethyl malonate anion in the presence of a catalytic amount of [(1-Me-allyl)PdCl]2 and (S)-(-)-BINAP proceeded enantiodistinctively to give both the nucleophilic substituted product (2S,4aS)-5 and the diene (R)-6 as the elimination product in considerable enantiomeric excesses.