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

Manjaly John Ajitha, Kuo-Wei Huang

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)10981-10985
Number of pages5
JournalOrg. Biomol. Chem.
Volume13
Issue number45
DOIs
StatePublished - 2015

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