Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 19, 2010
Previous Article Next Article

Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2Electronic supplementary information (ESI) available: Full details for reactions in Tables 1 and 2 with characterisation and spectra. See DOI: 10.1039/c0ob00102c

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
10 May 2010
Accepted
25 Jun 2010
First published
16 Aug 2010

Org. Biomol. Chem., 2010,8, 4444-4450
Article type
Paper

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

Social activity

Search articles by author

Spotlight

Advertisements