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Synfacts 2008(3): 0306-0306  
DOI: 10.1055/s-2008-1042718
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

ACDC-Epoxidation

Contributor(s): Benjamin List, Frank Lay
X. Wang, B. List*
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
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Publikationsdatum:
21. Februar 2008 (online)

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Significance

The authors employ asymmetric counteranion-directed catalysis (ACDC) for the enantioselective organocatalytic epoxidation of di- and trisubstituted α,β-unsaturated aldehydes 1. Dibenzylammonium salt 2 as catalyst together with tert-butyl hydroperoxide (3) as oxidant convert 1,2-disubstituted enals and β,β-disubstituted α,β-unsaturated aldehydes 1 into the corresponding 2,3-epoxyaldehydes 4 with high diastereo- and enantioselectivities.