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Issue 19, 2010
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Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2

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Abstract

A practical method for the multigram scale selective cis-dihydroxylation of electron deficient alkenes such as diethyl fumarate and N-alkyl and N-aryl-maleimides using H2O2 is described. High turnovers (>1000) can be achieved with this efficient manganese based catalyst system, prepared in situ from a manganese salt, pyridine-2-carboxylic acid, a ketone and a base, under ambient conditions. Under optimized conditions, for diethyl fumarate at least 1000 turnovers could be achieved with only 1.5 equiv. of H2O2 with d/l-diethyl tartrate (cis-diol product) as the sole product. For electron rich alkenes, such as cis-cyclooctene, this catalyst provides for efficient epoxidation.

Graphical abstract: Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2

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Publication details

The article was received on 10 May 2010, accepted on 25 Jun 2010 and first published on 16 Aug 2010


Article type: Paper
DOI: 10.1039/C0OB00102C
Citation: Org. Biomol. Chem., 2010,8, 4444-4450

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    Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2

    P. Saisaha, D. Pijper, R. P. van Summeren, R. Hoen, C. Smit, J. W. de Boer, R. Hage, P. L. Alsters, B. L. Feringa and W. R. Browne, Org. Biomol. Chem., 2010, 8, 4444
    DOI: 10.1039/C0OB00102C

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