Role of keto–enol tautomerization in a chiral phosphoric acid catalyzed asymmetric thiocarboxylysis of meso-epoxide: a DFT study

Handle URI:
http://hdl.handle.net/10754/622460
Title:
Role of keto–enol tautomerization in a chiral phosphoric acid catalyzed asymmetric thiocarboxylysis of meso-epoxide: a DFT study
Authors:
Ajitha, Manjaly John; Huang, Kuo-Wei ( 0000-0003-1900-2658 )
Abstract:
The 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.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division
Citation:
Ajitha 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.
Publisher:
Royal Society of Chemistry (RSC)
Journal:
Org. Biomol. Chem.
Issue Date:
15-Sep-2015
DOI:
10.1039/C5OB01473E
PubMed ID:
26393538
Type:
Article
ISSN:
1477-0520; 1477-0539
Sponsors:
Financial support was provided by King Abdullah University of Science and Technology.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorAjitha, Manjaly Johnen
dc.contributor.authorHuang, Kuo-Weien
dc.date.accessioned2017-01-02T09:28:32Z-
dc.date.available2017-01-02T09:28:32Z-
dc.date.issued2015-09-15en
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.en
dc.identifier.issn1477-0520en
dc.identifier.issn1477-0539en
dc.identifier.pmid26393538en
dc.identifier.doi10.1039/C5OB01473Een
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.en
dc.description.sponsorshipFinancial support was provided by King Abdullah University of Science and Technology.en
dc.publisherRoyal Society of Chemistry (RSC)en
dc.titleRole of keto–enol tautomerization in a chiral phosphoric acid catalyzed asymmetric thiocarboxylysis of meso-epoxide: a DFT studyen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalOrg. Biomol. Chem.en
kaust.authorAjitha, Manjaly Johnen
kaust.authorHuang, Kuo-Weien
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