Addition of silylated nucleophiles to α-oxoketenes

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Abstract

A general evaluation of silylated nucleophiles to intercept transient α-oxoketenes generated by microwave-assisted Wolff rearrangement of 2-diazo-1,3-dicarbonyl compounds is presented. Original scaffolds and synthetic intermediates are accessed in a rapid, efficient and easy-to-handle way. Mechanistic studies by DFT calculations and some post-functionalizations are discussed.

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Dudognon, Y., Presset, M., Rodriguez, J., Coquerel, Y., Bugaut, X., & Constantieux, T. (2016). Addition of silylated nucleophiles to α-oxoketenes. Chemical Communications, 52(14), 3010–3013. https://doi.org/10.1039/c5cc10217k

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