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Osmium‐Catalyzed Dihydroxylation of Olefins in Acidic Media: Old Process, New Tricks
Author(s) -
Dupau Philippe,
Epple Robert,
Thomas Allen A.,
Fokin Valery V.,
Sharpless K. Barry
Publication year - 2002
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/1615-4169(200206)344:3/4<421::aid-adsc421>3.0.co;2-f
Subject(s) - dihydroxylation , osmium , chemistry , catalysis , olefin fiber , citric acid , diol , organic chemistry , dissolution , enantioselective synthesis , ruthenium
A screen of over 500 diversely functionalized additives in osmium‐catalyzed dihydroxylation has uncovered that electron‐deficient olefins are converted into the corresponding diols much more efficiently when the pH of the reaction medium is maintained on the acidic side. Further studies have identified citric acid as the additive of choice, for it allows preparation of very pure diols in yields generally exceeding 90%. As described here, a much wider range of olefin classes can now be successfully dihydroxylated. The process is experimentally simple, in most cases involving little more than dissolving the reactants in water or a water/ tert ‐butyl alcohol mixture, stirring them, and filtering off the pure diol product.