Portal de Periódicos da CAPES

Manganese catalyzed cis-dihydroxylation of electron deficient alkenes with H2O2

2010; Royal Society of Chemistry; Volume: 8; Issue: 19 Linguagem: Inglês

10.1039/c0ob00102c

1477-0539

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

Polyoxometalates: Synthesis and Applications

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.