Organic Letters 2010-10-01

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)

Full Text: HTML

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.