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Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2

By Pattama Saisaha, Dirk Pijper, Ruben P. van Summeren, Rob Hoen, Christian Smit, Johannes W. de Boer, Ronald Hage, Paul L. Alsters, Ben L. Feringa and Wesley R. Browne

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.

Year: 2010
OAI identifier: oai:ub.rug.nl:dbi/4c877142005fd
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