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Asymmetric Counteranion-Directed Catalysis for the Epoxidation of Enals

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Wang,  Xing-Wang
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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Wang, X.-W., & List, B. (2008). Asymmetric Counteranion-Directed Catalysis for the Epoxidation of Enals. Angewandte Chemie International Edition, 47(6), 1119-1122. doi:10.1002/anie.200704185.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-90BF-C
Abstract
A new mode of chiral anion catalysis: A powerful chiral‐counteranion strategy for catalytic asymmetric epoxidations using the newly discovered catalyst 1 has been applied to the epoxidation of α,β‐unsaturated aldehydes together with tert‐butyl hydroperoxide as the oxidant (see scheme). Remarkably, this system provides the corresponding epoxides in high diastereo‐ and enantioselectivity for both di‐ and trisubstituted enals.