Asymmetric [3+2] Cycloaddition of Methyleneindolinones with N,N '-Cyclic Azomethine Imines Catalyzed by a N,N '-Dioxide Mg(OTf)(2) Complex

A highly efficient chiral N,N'-dioxide Mg-(OTf)(2) catalyst system has been developed for the asymmetric 1,3-dipolar cycloaddition between methyleneindolinones and N,N'-cyclic azomethine imines. The desired pyrazolidine products with contiguous quaternary tertiary stereocenters were obtain...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 80; no. 19; pp. 9691 - 9699
Main Authors Yin, Chengkai, Lin, Lili, Zhang, Dong, Feng, Juhua, Liu, Xiaohua, Feng, Xiaoming
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 02.10.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
STEREOCONTROL
LIGANDS
AMINES
CONSTRUCTION
CHEMISTRY
EARTH METAL-CATALYSTS
YLIDES
ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION
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Summary:A highly efficient chiral N,N'-dioxide Mg-(OTf)(2) catalyst system has been developed for the asymmetric 1,3-dipolar cycloaddition between methyleneindolinones and N,N'-cyclic azomethine imines. The desired pyrazolidine products with contiguous quaternary tertiary stereocenters were obtained in up to 99% yields with up to 99% ee and >19:1 dr under mild reaction conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b01760