Osmium Tetroxide Anchored to Porous Resins Bearing Residual Vinyl Groups: A Highly Active and Recyclable Solid for Asymmetric Dihydroxylation of Olefins
- 1 December 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (26) , 4685-4688
- https://doi.org/10.1021/ol027109r
Abstract
OsO4 was simply immobilized onto resins such as Amberlite XAD-4 or XAD-7 bearing residual vinyl groups. The resulting osmylated resins are air-stable, nonvolatile, and much easier to handle than their homogeneous counterpart (OsO4). Moreover, the resin-bound OsO4 exhibited excellent catalytic activity in the asymmetric dihydroxylation of olefins and was easily recovered and reused in five consecutive reactions without any significant decrease in product yield. Turnover time, however, was significantly increased for the fourth and fifth reactions.Keywords
This publication has 6 references indexed in Scilit:
- Catalytic Asymmetric Dihydroxylation of Olefins with New Catalysts: The First Example of Heterogenization of OsO42- by Ion-Exchange TechniqueJournal of the American Chemical Society, 2001
- Catalyst Immobilization: Solid SupportsPublished by Springer Nature ,1999
- Microencapsulated Osmium Tetraoxide. A New Recoverable and Reusable Polymer-Supported Osmium Catalyst for Dihydroxylation of OlefinsThe Journal of Organic Chemistry, 1998
- Functional polymers from (vinyl)polystyrene. Enzyme immobilization through a cysteinyl-S-ethyl spacerBiotechnology Techniques, 1995
- Preclusion of the “second cycle” in the osmium-catalyzed asymmetric dihydroxylation of olefins leads to a superior processTetrahedron Letters, 1990
- Osmium tetraoxide catalyzed vicinal hydroxylation of higher olefins by using hexacyanoferrate(III) ion as a cooxidantThe Journal of Organic Chemistry, 1990