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Direct Asymmetric α-Hydroxylation of Cyclic α-Branched Ketones through Enol Catalysis

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Shevchenko,  Grigory A.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Pupo,  Gabriele
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Shevchenko, G. A., Pupo, G., & List, B. (2019). Direct Asymmetric α-Hydroxylation of Cyclic α-Branched Ketones through Enol Catalysis. Synlett, 30(1), 49-53. doi:10.1055/s-0037-1611084.


Cite as: https://hdl.handle.net/21.11116/0000-0002-BF4A-5
Abstract
Enantiopure α-hydroxy carbonyl compounds are common scaffolds in natural products and pharmaceuticals. Although indirect approaches towards their synthesis are known, direct asymmetric methodologies are scarce. Herein, we report the first direct asymmetric α-hydroxylation of α-branched ketones through enol catalysis, enabling a facile access to valuable α-keto tertiary alcohols. The transformation, characterized by the use of nitrosobenzene as the oxidant and a new chiral phosphoric acid as the catalyst, delivers a good scope and excellent enantioselectivities.