Silica-Supported Tetramethylguanidine: An Efficient Solid Base for Aldol-Type Coupling of Aldehydes with Ethyl Diazoacetate

Pravin R. Likhar*, Sarabindu Roy, Moumita Roy, M. S. Subhas, M. Lakshmi Kantam

*Indian Institute of Chemical Technology, Inorganic & Physical Chemistry Division, Hyderabad 500007, India, Email: plikhariict.res.in

P. R. Likhar, S. Roy, M. Roy, M. S. Subhas, M. Lakshmi Kantam, Synlett, 2008, 1283-1286.

DOI: 10.1055/s-2008-1072769

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Abstract

Silica-supported tetramethylguanidine catalyst was prepared and effectively used in the aldol-type coupling of aldehydes with ethyl diazoacetate to afford the corresponding α-diazo-β-hydroxy esters in very good yields. The catalyst can be reused for a number of cycles with almost consistent activity by a simple filtration.

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Key Words

silica, tetramethylguanidine, aldol addition, α-hydroxy-β-di­azoesters, diazo compounds, reusable catalyst

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ID: J60-Y2008-1190