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Iridium-Catalyzed Asymmetric Addition of Thiophenols to Oxabenzonorbornadienes

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journal contribution
posted on 2016-09-29, 13:53 authored by Sifeng Li, Zhiwu Lu, Ling Meng, Jun Wang
A highly efficient asymmetric ring addition reaction of oxabenzo­norborna­dienes with thiophenols using an iridium/(S)-xyl-binap catalyst is developed. This catalyst system overcomes catalyst poisoning and background reactions and allows the formation of exclusive thiol addition products in high yields (up to 97% yield) with excellent enantioselectivities (up to 98% ee). Particularly noteworthy is that no competitive ring-opened side products are observed. X-ray crystal structure analysis confirmed the adduct is solely in the exo-configuration.

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