title: Stereoselective nucleophilic addition of PhSCF2 SiMe3 to chiral cyclic nitrones: asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines.
abstract: Fluoride-catalyzed nucleophilic addition of a difluoro(phenylsulfanyl)methyl group ("PhSCF2 ") generated from PhSCF2 SiMe3 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.
authors.affiliation: Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400 (Thailand).
authors.forename: Korkit
authors.initials: K
authors.lastname: Korvorapun
authors.forename: Darunee
authors.initials: D
authors.lastname: Soorukram
authors.forename: Chutima
authors.initials: C
authors.lastname: Kuhakarn
authors.forename: Patoomratana
authors.initials: P
authors.lastname: Tuchinda
authors.forename: Vichai
authors.initials: V
authors.lastname: Reutrakul
authors.forename: Manat
authors.initials: M
authors.lastname: Pohmakotr
mesh_terms: D002384:Catalysis; D054836:Indolizidines / Q000138:chemical synthesis*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*
chemical_list: D054836:Indolizidines; D009589:Nitrogen Oxides; C015388:nitrones
keywords: cyclization; fluorine; indolizidine; pyrrolizidine; radical reactions