Organic Letters
Organic Letters
5 years ago

Catalytic Asymmetric Electrophilic Cyanation of 3-Substituted Oxindoles

Catalytic Asymmetric Electrophilic Cyanation of 3-Substituted Oxindoles
Hongquan Yin, Jiashen Qiu, Peng Chen, Guirong Qi, Di Wu, Fu-Xue Chen, Pran Gopal Karmaker
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01756

DOI: 10.1021/acs.orglett.7b01756

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