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Stereoselective Synthesis of (E)‑3-Alkylideneoxindoles via Gold(I)-Catalyzed Cross-Coupling of 3‑Diazooxindoles with Diazoesters

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journal contribution
posted on 17.04.2020, 09:03 by Haiyang Cheng, Xinbo Yao, Shiwei Yin, Tao Wang, Zunting Zhang
A versatile gold­(I)-catalyzed cross-coupling reaction of 3-diazooxindoles with diazoesters has been presented, affording (E)-3-alkylideneoxindoles stereoselectively. Density functional theory calculations rationalized the chemo- and stereoselectivity of the reaction, which was in good agreement with experimental observations. In addition, (E)-3-alkylideneoxindoles were converted into their (Z)-isomers under UV-irradiation facilely, indicating the great advantage of this approach in stereoselective synthesis of both (E)- and (Z)-3-alkylideneoxindoles.