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