Chiral-Boron Complex-Catalyzed Asymmetric [3+2] Cycloaddition of 2′-Hydroxychalcones with N-2,2,2-Trifluoroethylisatin Ketimines

被引：0

作者：

Chai, Guo-Li ^{[1
]}

Wang, Xiao ^{[1
]}

Huang, Wei-Yu ^{[1
]}

Hou, Ya-Jing ^{[1
]}

Chang, Junbiao ^{[1
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, State Key Lab Antiviral Drugs, Pingyuan Lab, Xinxiang 453007, Henan, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 16期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; SPIROOXINDOLES;

D O I：

10.1021/acs.joc.4c01319

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient asymmetric [3 + 2] cycloaddition reaction of 2 '-hydroxychalcones with N-2,2,2-trifluoroethylisatin ketimines catalyzed by a (R)-3,3 '-I2-BINOL-boron complex was developed. A broad range of 3,2 '-pyrrolidinyl spirooxindole derivatives bearing a CF3-substituted pyrrolidine moiety with four contiguous stereocenters was prepared in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). This protocol had the characteristics of mild reaction conditions, high efficiency, and excellent stereocontrol.

引用

页码：11607 / 11619

页数：13

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