A survey of the reactivity of enoldiazo nucleophiles with a diverse series of in situ generated carbocations was performed. These couplings facilitate the rapid assembly of complex organodiazo compounds, which provide a template for the synthesis of a variety of important carbocyclic and heterocyclic ring systems. When combined with the array of coupling reactions that have been reported for enoldiazo compounds, the application these reagents present a unique opportunity to apply DOS-type strategies to rapidly access large and diverse libraries of medicinally interesting compounds. Furthermore, the use of interactive catalytic transformations makes this type of synthetic approach an economical and environmentally friendly way to prepare such libraries due to limited reagent requirements and low waste production.

Survey of enoldiazo nucleophilicity in selective C-C bond forming reactions for the synthesis of natural product-like frameworks

247th National Meeting (2014)

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