Synlett 2017; 28(06): 673-678
DOI: 10.1055/s-0036-1588363
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© Georg Thieme Verlag Stuttgart · New York

Thieme Chemistry Journals Awardees – Where Are They Now?
Stereoselective Cycloaddition of 2,2,2-Trifluorodiazoethane with α-Methylene-β-lactams: Facile Synthesis of Trifluoromethyl-Substituted Spirocyclic β-Lactams

Shen Li
Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China   Email: majun_an68@tju.edu.cn
,
Wen-Jie Cao
Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China   Email: majun_an68@tju.edu.cn
,
Jun-An Ma*
Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China   Email: majun_an68@tju.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 11 October 2016

Accepted after revision: 06 November 2016

Publication Date:
28 November 2016 (online)


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Abstract

The cycloadditions of 2,2,2-trifluorodiazoethane with α-methylene-β-lactams were investigated. The reaction proceeded via a [3+2] cycloaddition mode under metal-free conditions, whereas the use of an iron catalyst enabled a cyclopropanation to occur. This protocol offers a facile access to a broad range of trifluoromethyl containing spirocyclic β-lactams.

Supporting Information