Stereoselective Ag-Catalyzed 1,3-Dipolar Cycloaddition of Activated Trifluoromethyl-Substituted Azomethine Ylides

被引：55

作者：

Ponce, Alberto ^{[1
]}

Alonso, Ines ^{[1
]}

Adrio, Javier ^{[1
]}

Carretero, Juan C. ^{[1
]}

机构：

[1] Univ Autonoma Madrid, Fac Ciencias, Dept Quim Organ, E-28049 Madrid, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 14期

关键词：

asymmetric catalysis; cycloaddition; fluorinated pyrrolidines; silver; ylides; ASYMMETRIC 3+2 CYCLOADDITION; ENANTIOSELECTIVE SYNTHESIS; IMINO ESTERS; PYRROLIDINES; CONSTRUCTION; ALKALOIDS; CHEMISTRY; NITROALKENES; COMPLEXES; FLUORINE;

D O I：

10.1002/chem.201504869

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A silver-catalyzed 1,3-dipolar cycloaddition of fluorinated azomethine ylides and activated olefins is reported. The reaction offers a straightforward and atom-economical procedure for the preparation of fluorinated pyrrolidines. Broad scope and high levels of diastereoselectivity have been achieved simply by using AgOAc/PPh3 as the catalyst system. The high efficiency of the cycloaddition relies on the presence of a metal-coordinating group on the imine moiety, such as an ester or heteroaryl group. The asymmetric version of the cycloaddition has been developed by using Taniaphos as a chiral ligand.

引用

页码：4952 / 4959

页数：8

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