Keereewan S.Kuhakarn C.Leowanawat P.Saithong S.Reutrakul V.Soorukram D.Mahidol University2023-06-182023-06-182022-12-02Journal of Organic Chemistry Vol.87 No.23 (2022) , 15963-1598500223263https://repository.li.mahidol.ac.th/handle/20.500.14594/84136A 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.ChemistryArticleSCOPUS10.1021/acs.joc.2c020982-s2.0-8514195508815206904