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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Michael addition/pericyclization/rearrangement--a multicomponent strategy for the synthesis of substituted
1Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA.
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.
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