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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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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