“On Water” Direct Organocatalytic Cyanoarylmethylation of Isatins for the Diastereoselective Synthesis of 3-Hydroxy-3-cyanomethyl Oxindoles | Zendy

Yong Zhang | Zendy; Liang Luo | Zendy; Jin Ge | Zendy; Su-Qiong Yan | Zendy; Yan-Xin Peng | Zendy; Yurong Liu | Zendy; Jinxiang Liu | Zendy; Chong Liu | Zendy; Tianqiong Ma | Zendy; Haiqing Luo | Zendy

Open Access

“On Water” Direct Organocatalytic Cyanoarylmethylation of Isatins for the Diastereoselective Synthesis of 3-Hydroxy-3-cyanomethyl Oxindoles

Author(s) -

Yong Zhang,

Liang Luo,

Jin Ge,

Su-Qiong Yan,

Yan-Xin Peng,

Yurong Liu,

Jinxiang Liu,

Chong Liu,

Tianqiong Ma,

Haiqing Luo

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.8b03194

Subject(s) - acetonitrile , aryl , organocatalysis , chemistry , catalysis , combinatorial chemistry , organic chemistry , enantioselective synthesis , alkyl

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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