Organic & Biomolecular Chemistry 2012-08-21

Michael addition/pericyclization/rearrangement--a multicomponent strategy for the synthesis of substituted resorcinols.

Yu Liu, Michael P Doyle

Index: Org. Biomol. Chem. 10(31) , 6388-94, (2012)

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Abstract

The combination of methyl 3,7-dioxo-2-diazo-4-octenoate from the zinc triflate catalyzed Mukaiyama-Michael reaction of methyl 3-tert-butylsilyloxy-2-diazobutenoate and 4-methoxy-3-buten-2-one with Michael acceptors (methyl vinyl ketone, N-phenylmaleimide, β-nitrovinylarenes) in the presence of a catalytic amount of base provides convenient access to highly substituted resorcinol derivatives. This transformation is achieved in an efficient one-pot multi-component transformation by the sequential addition of the reagents.