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Copper-Catalyzed Coupling of 2-Siloxy-1-alkenes and Diazocarbonyl Compounds: Approach to Multisubstituted Furans, Pyrroles, and Thiophenes

Wei Wen Tan and Naohiko Yoshikai*

*Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore, Email: nyoshikaintu.edu.sg

W. W. Tan, N. Yoshikai, J. Org. Chem., 2016, 81, 5566-5573.

DOI: 10.1021/acs.joc.6b00904 (free Supporting Information)


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Abstract

A copper(II)-catalyzed cyclization reaction of silyl enol ethers derived from methyl ketones with α-diazo-β-ketoesters or α-diazoketones provides 2-siloxy-2,3-dihydrofuran derivatives. These cyclization products serve as versatile 1,4-diketone surrogates, allowing facile in situ preparation of 2,3,5-trisubstituted furans, pyrroles, and thiophenes.

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Key Words

furans, pyrroles


ID: J42-Y2016