Platinum-Catalyzed Asymmetric Ring-Opening Reactions of Oxabenzonorbornadienes with Phenols

A platinum­(II)-catalyzed asymmetric
ring opening of oxabenzonorbornadienes
with phenols was developed, which afforded the corresponding cis-2-(un)­substituted phenoxy-1,2-dihydronaphthalen-1-ol
products rather than the trans ones in excellent
yields (up to 99%) with moderate to good enantioselectivities (up
to 87% ee) under mild conditions. In addition, the cis-configuration of product 2b was confirmed by X-ray
diffraction analysis. Based on the results, a potential mechanism
for the present catalytic reaction was proposed.