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

被引：14

作者：

Zhang, Yong ^{[1
]}

Luo, Liang ^{[1
]}

Ge, Jin ^{[1
]}

Yan, Su-Qiong ^{[1
]}

Peng, Yan-Xin ^{[1
]}

Liu, Ya-Ru ^{[1
]}

Liu, Jin-Xiang ^{[1
]}

Liu, Chong ^{[3
]}

Ma, Tianqiong ^{[2
]}

Luo, Hai-Qing ^{[1
]}

机构：

[1] Gannan Normal Univ, Key Lab Organopharmaceut Chem, Ganzhou 341000, Peoples R China

[2] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[3] Delft Univ Technol, Dept Chem Engn, Inorgan Syst Engn Grp, Van der Maasweg 9, NL-2629 HZ Delft, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 07期

基金：

中国国家自然科学基金;

关键词：

NUCLEOPHILIC-ADDITION REACTIONS; CATALYTIC ASYMMETRIC ADDITION; HENRY NITROALDOL REACTIONS; ORGANIC-REACTIONS; ALDOL REACTION; UNSATURATED NITRILES; GREEN CHEMISTRY; ALLYL CYANIDE; ON-WATER; CONSTRUCTION;

D O I：

10.1021/acs.joc.8b03194

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4000 / 4008

页数：9

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