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dc.contributor.authorFristrup, P.
dc.contributor.authorLassen, P.
dc.contributor.authorTanner, D.
dc.contributor.authorJalkanen, Karl
dc.date.accessioned2017-01-30T15:17:49Z
dc.date.available2017-01-30T15:17:49Z
dc.date.created2009-03-05T00:58:34Z
dc.date.issued2008
dc.identifier.citationFristrup, Peter and Lassen, Peter Rygaard and Tanner, David and Jalkanen, K. J.. 2008. Direct determination of absolute configuration: a vibrational circular dichroism study on dimethyl-substituted phenyloxiranes synthesized by Shi epoxidation. Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta) 119: pp. 133-142.
dc.identifier.urihttp://hdl.handle.net/20.500.11937/45018
dc.identifier.doi10.1007/s00214-006-0186-1
dc.description.abstract

The three possible dimethylsubstituted phenyloxiranes (cis, trans and geminal) were synthesized in both racemic (mCPBA) and enantiomerically enriched forms (Shi epoxidation) and subjected to a vibrational circular dichroism study. The experimental spectra were compared to theoretical spectra obtained using DFT/B3LYP calculations, and the differences between experiment and theory are discussed. The absolute configuration at the benzylic position was established as being (R), (S) and (R) for the cis, trans and geminal dimethylsubstituted phenyloxiranes, respectively. In all three cases the configuration of the major enantiomer was in accordance with a simple transition state model based on the spiro reaction mode.

dc.publisherSpringer Berlin
dc.subjectDFT
dc.subjectcalculations
dc.subjectEpoxidation
dc.subjectVibrational circular dichroism
dc.subjectAbsolute configuration
dc.subjectAsymmetric catalysis
dc.titleDirect determination of absolute configuration: a vibrational circular dichroism study on dimethyl-substituted phenyloxiranes synthesized by Shi epoxidation
dc.typeJournal Article
dcterms.source.volume119
dcterms.source.startPage133
dcterms.source.endPage142
dcterms.source.issn14322234
dcterms.source.titleTheoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta)
curtin.note

The original publication is available at : www.springerlink.com

curtin.accessStatusFulltext not available
curtin.facultyDepartment of Applied Chemistry
curtin.facultySchool of Science and Computing
curtin.facultyFaculty of Science and Engineering


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