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Microwave-assisted, regioselective, Petasis olefination of unsymmetrical oxalates. Formation of pyruvate-based enol ethers and enamines
Authors:Matthew J Cook
Institution:School of Chemistry, University of Bristol, Bristol BS8 1TS, United Kingdom
Abstract:The Petasis olefination of unsymmetrical oxalates and oxalate monoesters/monoamides (tert-BuO2CC(O)X, where X = OR, NR2) is highly regioselective and provides pyruvate-based enol ether and enamine derivatives. The olefination step occurs under conventional thermal conditions, but is dramatically improved--shorter reaction times and higher yields--when promoted by microwave irradiation.
Keywords:Petasis reagent  Olefination  Pyruvates  Enamines  Enol ethers
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