Chiral-Boron-Complex-Catalyzed Asymmetric [3+2] Cycloaddition of β-Trifluoromethyl α,β-Unsaturated Ketones with N,N′-Cyclic Azomethine Imines

被引：2

作者：

Liu, Rui-Hao ^{[1
]}

Chai, Guo-Li ^{[1
]}

Wang, Xiao ^{[1
]}

Deng, Hong-Yu ^{[1
]}

Chang, Junbiao ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 23期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; CONJUGATE ADDITION; ALKENYLBORONIC ACIDS; METHYLENEINDOLINONES; DERIVATIVES;

D O I：

10.1021/acs.joc.3c02106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The (R)-3,3 '-(3,5-(CF3)2-C6H3)2-BINOL-boron-complex-catalyzed asymmetric 1,3-dipolar cycloaddition of beta-trifluoromethyl alpha,beta-unsaturated ketone with N,N '-cyclic azomethine imines was developed to afford N,N '-bicyclic pyrazolidine derivatives bearing a stereogenic carbon center containing CF3 motifs in high yields with excellent diastereo- and enantioselectivities (up to >20:1 dr, and >99% ee). This catalytic system features mild reaction conditions, high efficiency, and a broad substrate scope.

引用

页码：16566 / 16580

页数：15

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