American Chemical Society
jo5b00065_si_001.pdf (1.23 MB)

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

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journal contribution
posted on 2015-03-06, 00:00 authored by Ling Meng, Wen Yang, Xuejing Pan, Meng Tao, Guo Cheng, Sanyong Wang, Heping Zeng, Yuhua Long, Dingqiao Yang
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.