Diastereoselective Addition of PhSCF<inf>2</inf>SiMe<inf>3</inf>to Chiral N- tert-Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles

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dc.contributor.authorKeereewan S.
dc.contributor.authorKuhakarn C.
dc.contributor.authorLeowanawat P.
dc.contributor.authorSaithong S.
dc.contributor.authorReutrakul V.
dc.contributor.authorSoorukram D.
dc.contributor.otherMahidol University
dc.date.accessioned2023-06-18T16:56:54Z
dc.date.available2023-06-18T16:56:54Z
dc.date.issued2022-12-02
dc.description.abstractA convenient and efficient synthetic strategy to prepare enantioenriched gem-difluoromethylenated spiro-pyrrolidinyl and spiro-piperidinyl oxindoles is described. Fluoride-mediated diastereoselective nucleophilic addition of PhSCF2SiMe3to chiral N-tert-butanesulfinyl ketimines derived from isatins was a key step and provided diastereomeric adducts, which were readily separable. Removal of the chiral sulfinyl group followed by structural manipulation afforded chiral gem-difluoromethylenated spiro-pyrrolidinyl and spiro-piperidinyl oxindoles.
dc.identifier.citationJournal of Organic Chemistry Vol.87 No.23 (2022) , 15963-15985
dc.identifier.doi10.1021/acs.joc.2c02098
dc.identifier.eissn15206904
dc.identifier.issn00223263
dc.identifier.scopus2-s2.0-85141955088
dc.identifier.urihttps://repository.li.mahidol.ac.th/handle/20.500.14594/84136
dc.rights.holderSCOPUS
dc.subjectChemistry
dc.titleDiastereoselective Addition of PhSCF<inf>2</inf>SiMe<inf>3</inf>to Chiral N- tert-Butanesulfinyl Ketimines Derived from Isatins: Synthesis of Enantioenriched gem-Difluoromethylenated Spiro-pyrrolidinyl and Spiro-piperidinyl Oxindoles
dc.typeArticle
mu.datasource.scopushttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85141955088&origin=inward
oaire.citation.endPage15985
oaire.citation.issue23
oaire.citation.startPage15963
oaire.citation.titleJournal of Organic Chemistry
oaire.citation.volume87
oairecerif.author.affiliationMahidol University
oairecerif.author.affiliationPrince of Songkla University

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