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Synthesis 2018; 50(12): 2367-2384
DOI: 10.1055/s-0036-1591554
DOI: 10.1055/s-0036-1591554
paper
Synthesis of 1-Acyl-2-vinylcyclopropanes: Utilizing Copper-Carbenoid versus Sulfur Ylide Methodology
Generous financial support from the Ministerium für Wissenschaft, Forschung und Kunst des Landes Baden-Württemberg, the Deutsche Forschungsgemeinschaft (shared instrumentation grants for 700 MHz NMR) and the Fonds der Chemischen Industrie is gratefully acknowledged.Further Information
Publication History
Received: 18 December 2017
Accepted after revision: 22 February 2018
Publication Date:
27 March 2018 (online)
Abstract
The synthesis of a range of racemic 1-acyl-2-vinylcyclopropanes by using two different methodologies is studied. We have developed a copper-catalyzed process for converting diazoketones into 1-acyl-2-vinylcyclopropanes and a sulfur-ylide-mediated procedure which allows, in only two steps, a simplified access to 1-acyl-2-vinylcyclopropanes with alkyl or aryl substituents on the alkene moiety.
Key words
vinylcyclopropanes - cyclopropanation - cyclic enones - sulfur ylides - copper catalysis - [2+1] annulations - diazoketonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591554.
- Supporting Information
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