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Catalytic Asymmetric Hydroperoxidation of α,β-Unsaturated Ketones: An Approach to Enantiopure Peroxyhemiketals, Epoxides, and Aldols

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Reisinger,  Corinna M.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wang,  Xingwang
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

Reisinger, C. M., Wang, X., & List, B. (2008). Catalytic Asymmetric Hydroperoxidation of α,β-Unsaturated Ketones: An Approach to Enantiopure Peroxyhemiketals, Epoxides, and Aldols. Angewandte Chemie International Edition, 47(42), 8112-8115. doi:10.1002/anie.200803238.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-9079-8
Abstract
Efficient, selective: The primary amine salt 1 derived from quinine efficiently catalyzes the highly enantioselective hydroperoxidation of α,β‐unsaturated ketones furnishing stable and isolable cyclic peroxyhemiketals in enantiopure form. The versatility of the peroxyhemiketals was demonstrated with the syntheses of aldols and epoxides from α,β‐unsaturated ketones and hydrogen peroxide (see scheme).