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dc.contributor.authorAjitha, Manjaly John
dc.contributor.authorHuang, Kuo-Wei
dc.date.accessioned2017-01-02T09:28:32Z
dc.date.available2017-01-02T09:28:32Z
dc.date.issued2015
dc.identifier.citationAjitha MJ, Huang K-W (2015) Role of keto–enol tautomerization in a chiral phosphoric acid catalyzed asymmetric thiocarboxylysis of meso-epoxide: a DFT study. Org Biomol Chem 13: 10981–10985. Available: http://dx.doi.org/10.1039/C5OB01473E.
dc.identifier.issn1477-0520
dc.identifier.issn1477-0539
dc.identifier.pmid26393538
dc.identifier.doi10.1039/C5OB01473E
dc.identifier.urihttp://hdl.handle.net/10754/622460
dc.description.abstractThe mechanism of a chiral phosphoric acid catalyzed thiocarboxylysis of meso-epoxide was investigated by density functional theory (DFT) calculations (M06-2X). The nucleophilic ring opening of epoxide by thiobenzoic acid was found to proceed via a concerted termolecular transition state with a simultaneous dual proton transfer to yield the β-hydroxy thioester product. Electrostatic interactions together with the steric environment inside the chiral catalyst play an important role in determining the enantioselectivity of the reaction.
dc.description.sponsorshipFinancial support was provided by King Abdullah University of Science and Technology.
dc.publisherRoyal Society of Chemistry (RSC)
dc.titleRole of keto–enol tautomerization in a chiral phosphoric acid catalyzed asymmetric thiocarboxylysis of meso-epoxide: a DFT study
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalOrganic & Biomolecular Chemistry
kaust.personAjitha, Manjaly John
kaust.personHuang, Kuo-Wei


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