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

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Organic & biomolecular chemistry, ISSN: 1477-0539, Vol: 13, Issue: 45, Page: 10981-5

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Ajitha, Manjaly John, Huang, Kuo-Wei
Royal Society of Chemistry (RSC), The Royal Society of Chemistry
Chemistry, Biochemistry, Genetics and Molecular Biology
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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.

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