Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Ylides with Fluorinated Imines: The Expanded Scope and Mechanism Insights

被引：25

作者：

Wei, Liang ^{[1
]}

Li, Qing-Hua ^{[1
]}

Wang, Chun-Jiang ^{[1
,2
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China

[2] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 230021, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 19期

基金：

中国博士后科学基金;

关键词：

SELECTIVE 3+2 CYCLOADDITION; IMIDAZOLIDINES; CONSTRUCTION; ACCESS; TRIFLUOROMETHYLATION; HETEROCYCLES; IMINOESTERS; DERIVATIVES; CATALYSIS; TROPONE;

D O I：

10.1021/acs.joc.8b01743

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The mechanism of the Cu(I)/(S,R-p)-PPFOMe-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with fluorinated aldimines has been studied using labeling experiments, control experiments, and linear effect experiments, which clearly ruled out the 1,3-DC/epimerization pathways and explained the unusal exo'-selective stereochemistry. This protocol allows for the preparation of a series of highly functionalized fluorinated imidazolidines in good yields with excellent stereoselectivities. Moreover, the current methods have been successfully extended to synthesize more challenging imidazolidines bearing a CF(3-)containing quaternary stereogenic center via the endo-selective 1,3-DC of azomethine ylides with trifluorinated ketimine under identical reaction conditions.

引用

页码：11814 / 11824

页数：11

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