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Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/4871
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dc.contributor.authorHamon, David P. G.en
dc.contributor.authorTuck, Kellie Louiseen
dc.contributor.authorChristie, Hamish Saulen
dc.date.issued2001en
dc.identifier.citationTetrahedron, 2001; 57(46):9499-9508en
dc.identifier.issn0040-4020en
dc.identifier.urihttp://hdl.handle.net/2440/4871-
dc.descriptionAvailable online 5 November 2001.en
dc.description.abstractThe requirements for a highly selective kinetic resolution with the Sharpless asymmetric dihydroxylation (AD) reaction were investigated with a number of alkene substrates. It was found that with 1-phenyl-4-tert-butylcyclohexene enantioselectivity is very high, yet diastereoselectivity is poor and kinetic resolution is ineffective. With 5-methyl-2-phenylbicyclo[3.2.0]heptan-2-ene both diastereoselectivity and enantioselectivity are high and kinetic resolution is effective. It was discovered that the transition state for the product-determining step in the Sharpless AD reaction is not product-like, and effective kinetic resolution can occur when one face of a chiral alkene is hindered. It was discovered that the transition state for the product-determining step in the Sharpless asymmetric dihydroxylation reaction is not product-like, and effective kinetic resolution can occur when one face of a chiral alkene is hindered.en
dc.description.statementofresponsibilityDavid P.G Hamon, Kellie L Tuck and Hamish S Christieen
dc.language.isoenen
dc.publisherPergamon-Elsevier Science Limiteden
dc.rightsCopyright © 2001 Elsevier Science Ltd. All rights reserved.en
dc.subjectsharpless asymmetric dihydroxylation ; kinetic resolutions ; transition stateen
dc.titleAn investigative study of kinetic resolutions by the Sharpless asymmetric dihydroxylation reactionen
dc.typeJournal articleen
dc.contributor.schoolSchool of Chemistry and Physics : Chemistryen
dc.identifier.doi10.1016/S0040-4020(01)00948-6en
Appears in Collections:Chemistry publications

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