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Synfacts 2005(0): 0076-0076  
DOI: 10.1055/s-2005-869988
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes

Contributor(s): Hisashi Yamamoto, Matthew Boxer
M. Marigo, J. Franzen, T. B. Poulsen, W. Zhuang, K. A. Jørgensen*
Aarhus University, Denmark
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Publikationsdatum:
20. Juli 2005 (online)

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Significance

Epoxidation has long been an important synthetic transformation in synthetic chemistry. This represents the first direct formation of α,β-epoxy aldehydes which, importantly, was achieved under simple and mild conditions. Hydrogen peroxide was found to be the oxidant of choice while t-BuOOH, cumene hydroperoxide, and urea hydrogen peroxide gave similar results, but m-CPBA gave almost no conversion (< 3%).