The highly selective transformations made possible by metal catalyzed diazo decomposition in complex environments have provided efficient pathways to important natural products and biologically relevant small molecules.  The discovery of new reactions with metal carbenes has been further advanced by novel synthetic methodologies that take advantage of the stability and reactivities of a-diazo-�-ketoesters to rapidly assemble highly functionalized diazo compounds, which have traditionally been synthesized by more cumbersome means.  We will present a novel synthetic strategy in the chemistry of diazo compounds, which takes advantage of the previously unknown ability of diazoacetoacetate enones to behave as general Michael acceptors under Lewis acid catalyzed conditions to provide complex diazo compounds with remarkable efficiency and modularity.

Diazoacetate enones as a novel and modular entry into complex diazo compounds: Application to the synthesis of natural product-like carbocyclic and heterocyclic frameworks

244th National Meeting (2012)

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