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Catalytic Asymmetric Electrophilic Cyanation of 3‑Substituted Oxindoles

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journal contribution
posted on 20.07.2017, 12:22 by Jiashen Qiu, Di Wu, Pran Gopal Karmaker, Guirong Qi, Peng Chen, Hongquan Yin, Fu-Xue Chen
The first example of catalytic asymmetric electrophilic cyanation of 3-substituted oxindoles has been achieved using readily accessible 4-acetylphenyl cyanate as the cyano source. Thus, a series of all-carbon quaternary center 3-aryl-3-cyano oxindoles were prepared using a zinc complex of a chiral pincer ligand as the catalyst in high yields (up to 95%) and excellent enantioselectivities (up to >99% ee) in the presence of 4 Å MS and 2,6-lutidine in THF at 0 °C.

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