Platinum-Catalyzed Asymmetric Ring-opening Reaction of Oxabenzonorbornadiene with Terminal Alkynes

A novel platinum-catalyzed asymmetric ring-opening reaction of oxabenzonorbornadiene with terminal alkynes is described.The reaction affords optically active cis-2-alkynyl-1,2-dihydronaphthalen-1-ols in moderate yields with good enantioselectivity in the presence of catalytic amounts of Pt(COD)Cl_(2)/(S)-BINAP and an excess of zinc powder.The products were obtained exclusively with the relative cis-configuration of the ring substituents and the prevalent(1R,2S)-configuration of the stereocenters,as determined by single crystal X-ray diffraction analysis.