Highly effective transition structure designed catalyst for the enantio- and position-selective dihydroxylation of polyisoprenoids.
[structure: see text] The chiral monocinchona derivative shown, synthesized in one step from two efficiently prepared chiral building blocks, was designed under mechanistic guidance as a catalyst for the enantio- and position-selective dihydroxylation of the terminal isopropylidene group of polyisoprenoids. Its efficacy as a synthetic reagent for this purpose was demonstrated for several different substrates.
Corey
E J
EJ
Department of Chemistry and Chemical Biology Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA. corey@chemistry.harvard.edu
Zhang
J
J
D000475:Alkenes / Q000737:chemistry; D002930:Cinchona Alkaloids / Q000138:chemical synthesis*; D004224:Diterpenes / Q000138:chemical synthesis / Q000737:chemistry*; D006900:Hydroxylation; D009993:Osmium Tetroxide / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D002930:Cinchona Alkaloids; D004224:Diterpenes; C013658:propylene; D009993:Osmium Tetroxide