Unusual reaction of aryldiazoacetates with enamines: highly effective synthesis of c-ketoesters
Tetrahedron Letters 45(2004)6365-6367，-0001，（）：
The reaction of aryldiazoacetates with enamines catalyzed by copper and rhodium complexes provided c-ketoesters in good yields. Careful analysis of the crude reaction mixture revealed a substituted enamine as the primary product, which was hydrolyzed over silica gel to give a c-ketoester as the final product. A reaction mechanism involving nucleophilic addition of an enamine to a metal carbene and subsequent hydrogen transfer was proposed.
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