"on Water" Direct Organocatalytic Cyanoarylmethylation of Isatins for the Diastereoselective Synthesis of 3-Hydroxy-3-cyanomethyl Oxindoles

Journal Article (2019)
Author(s)

Y. Zhang (Gannan Normal University, Ganzhou)

Liang Luo (Gannan Normal University, Ganzhou)

Jin Ge (Gannan Normal University, Ganzhou)

Su Qiong Yan (Gannan Normal University, Ganzhou)

Yan Xin Peng (Gannan Normal University, Ganzhou)

Ya Ru Liu (Gannan Normal University, Ganzhou)

Jin Xiang Liu (Gannan Normal University, Ganzhou)

Chong Liu (TU Delft - ChemE/Inorganic Systems Engineering)

Tianqiong Ma (Lanzhou University)

More authors (External organisation)

Research Group
ChemE/Inorganic Systems Engineering
Copyright
© 2019 Y. Zhang, Liang Luo, Jin Ge, Su Qiong Yan, Yan Xin Peng, Ya Ru Liu, Jin Xiang Liu, C. Liu, Tianqiong Ma, More Authors
DOI related publication
https://doi.org/10.1021/acs.joc.8b03194
More Info
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Publication Year
2019
Language
English
Copyright
© 2019 Y. Zhang, Liang Luo, Jin Ge, Su Qiong Yan, Yan Xin Peng, Ya Ru Liu, Jin Xiang Liu, C. Liu, Tianqiong Ma, More Authors
Research Group
ChemE/Inorganic Systems Engineering
Issue number
7
Volume number
84
Pages (from-to)
4000-4008
Reuse Rights

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Abstract

An "on water" organocatalytic cyanoarylmethylation of aryl acetonitrile to isatins is developed, giving products in high yields and up to excellent diastereoselectivities. A remarkable enhancement of reaction rates and diastereoselectivities by water was observed under mild conditions. Moreover, this approach provides a highly efficient and environmentally benign access to thermodynamic 3-hydroxy-3-cyanomethyl oxindoles.

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