Pericyclic reaction of a zwitterionic salt of an enedione-diazoester. A novel strategy for the synthesis of highly functionalized resorcinols.

Yu Liu, Kanwarpal Bakshi, Peter Zavalij, Michael P Doyle

Index: Org. Lett. 12(19) , 4304-7, (2010)

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Abstract

Enedione-diazoesters formed from 3-TBSO-2-diazo-3-butenoates undergo base-catalyzed pericyclization that with dinitrogen extrusion and methyl migration provide a novel and efficient route to 2-carboalkoxyresorcinols. Intercepting the intermediate enolate anion with methyl vinyl ketone leads to the corresponding 4-substituted 2-carboalkoxyresorcinol and suggests generalization of this methodology.