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Vol. 23 No. 4 (2011): Vol 23 Issue 4

Sc(OTf)3-Catalyzed Tandem [3+2] Cycloaddition/Nucleophilic Ring-Opening Reaction of Cyclopropane 1,1-Diesters with Azomethine Ylides

J. Fang
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. China
B. Hu
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. China
J. Ren
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. China
Z.-W. Wang
State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P.R. China

Corresponding Author(s) : Z.-W. Wang

wzwrj@nankai.edu.cn

Asian Journal of Chemistry, Vol. 23 No. 4 (2011): Vol 23 Issue 4

Abstract

A new Sc(OTf)3-catalyzed tandem reaction combined with a dimerized self-[3+2] cycloaddition of azomethine ylide and a nucleophilic ring-opening of cyclopropane 1,1-diester has been developed. A series of polyfunctionalized imidazolidine derivatives were synthesized by this reaction (Yield 44-77 %). In some cases, this tandem reaction was also accompanied by a cross- [3+2] cycloaddition of cyclopropane 1,1-diester with imine.

Keywords

Lewis acid Imidazolidine Cyclopropane 1,1-diesters Tandem
(1)
Fang, J.; Hu, B.; Ren, J.; Wang, Z.-W. Sc(OTf)3-Catalyzed Tandem [3+2] Cycloaddition Nucleophilic Ring-Opening Reaction of Cyclopropane 1,1-Diesters With Azomethine Ylides. ajc 2010, 23, 1479-1487.
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