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Synlett 2017; 28(06): 673-678
DOI: 10.1055/s-0036-1588363
DOI: 10.1055/s-0036-1588363
letter
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Stereoselective Cycloaddition of 2,2,2-Trifluorodiazoethane with α-Methylene-β-lactams: Facile Synthesis of Trifluoromethyl-Substituted Spirocyclic β-Lactams
Further Information
Publication History
Received: 11 October 2016
Accepted after revision: 06 November 2016
Publication Date:
28 November 2016 (online)


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.
Key words
2,2,2-trifluorodiazoethane - α-methylene-β-lactam - spirocyclic β-lactam - [3+2] cycloaddition - cyclopropanationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588363.
- Supporting Information