Rh-catalyzed desymmetrization of α-quaternary centers by isomerization-hydroacylation

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Abstract

We describe a Rh-catalyzed desymmetrization of all-carbon quaternary centers from α,α-bis(allyl)aldehydes by a cascade featuring isomerization and hydroacylation. This desymmetrization competes with two other novel olefin functionalizations that are triggered by C-H bond activation, including carboacylation and bisacylation. A BIPHEP ligand promotes enantioselective formation of α-vinylcyclopentanones. Mechanistic studies support irreversible and enantioselective olefin-isomerization followed by olefin-hydroacylation.

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Park, J. W., Kou, K. G. M., Kim, D. K., & Dong, V. M. (2015). Rh-catalyzed desymmetrization of α-quaternary centers by isomerization-hydroacylation. Chemical Science, 6(8), 4479–4483. https://doi.org/10.1039/c5sc01553g

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