Stereoselective nucleophilic addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to chiral cyclic nitrones: Asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines

Korkit KorvorapunDarunee SoorukramChutima KuhakarnPatoomratana TuchindaVichai ReutrakulManat PohmakotrMahidol University2018-11-232018-11-232015-01-01Chemistry - An Asian Journal. Vol.10, No.4 (2015), 948-9681861471X186147282-s2.0-84925590476https://repository.li.mahidol.ac.th/handle/20.500.14594/35763© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Fluoride-catalyzed nucleophilic addition of a difluoro(phenylsulfanyl)methyl group ("PhSCF2") generated from PhSCF2SiMe3 to nitrones was accomplished in satisfactory yields. High diastereoselectivities were observed with chiral polyoxygenated cyclic nitrones to provide the corresponding adducts, which were further manipulated to afford gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines.Mahidol UniversityChemistryStereoselective nucleophilic addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to chiral cyclic nitrones: Asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidinesArticleSCOPUS10.1002/asia.201403023