New osmium-based reagent for the dihydroxylation of alkenes

Timothy J. Donohoe, Robert M. Harris, Sam Butterworth, Jeremy N. Burrows, Andrew Cowley, Jeremy S. Parker

Research output: Contribution to journalArticlepeer-review

Abstract

The cis dihydroxylation of alkenes is most efficiently accomplished by reaction with osmium tetroxide. Recently, the expense and toxicity of osmium tetroxide have led to a number of attempts to harness alternative osmium-based reagents, including microencapsulation and solid support techniques. We describe here the development of a new nonvolatile, stable, and recoverable osmium-based reagent devised for the stoichiometric cis dihydroxylation of alkenes. Although attempts to make this new dihydroxylation work with catalytic amounts of this reagent were unsuccessful, we did develop a sensitive test for free osmium tetroxide leached from the reagent in situ: this test may well have uses in probing future applications of derivatized osmium reagents.

Original languageEnglish
Pages (from-to)4481-4489
Number of pages9
JournalJournal of Organic Chemistry
Volume71
Issue number12
DOIs
Publication statusPublished - 9 Jun 2006

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