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

Journal article (2019)

Authors

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
C. Liu ChemE/Inorganic Systems Engineering - AS
Tianqiong Ma Lanzhou University
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Research Group
ChemE/Inorganic Systems Engineering (AS) (TU Delft)
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: https://doi.org/10.1021/acs.joc.8b03194
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Published Date

2019

Language

English

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Faculty

Applied Sciences

Department

ChemE/Chemical Engineering

Research Group

ChemE/Inorganic Systems Engineering

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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