title: Synthesis of gem-difluoromethylenated bicyclo[m.n.0]alkan-1-ols and their ring-expansion to gem-difluoromethylenated macrocyclic lactones.
abstract: Fluoride-catalyzed stereoselective nucleophilic addition of PhSCF(2)SiMe(3) (1) to α-carboethoxycycloalkanones 2 followed by intramolecular radical cyclization of the resulting cis-3 adduct afforded the corresponding gem-difluoromethylenated bicyclic compounds 4, which underwent ring-expansion followed by the Baeyer-Villiger-type oxidation of the resulting macrocyclic ketone intermediates to give gem-difluoromethylenated macrocyclic lactones 5.
authors.affiliation: Center of Excellence for Innovation in Chemistry and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand.
authors.forename: Teerachai
authors.initials: T
authors.lastname: Punirun
authors.forename: Krisana
authors.initials: K
authors.lastname: Peewasan
authors.forename: Chutima
authors.initials: C
authors.lastname: Kuhakarn
authors.forename: Darunee
authors.initials: D
authors.lastname: Soorukram
authors.forename: Patoomratana
authors.initials: P
authors.lastname: Tuchinda
authors.forename: Vichai
authors.initials: V
authors.lastname: Reutrakul
authors.forename: Palangpon
authors.initials: P
authors.lastname: Kongsaeree
authors.forename: Samran
authors.initials: S
authors.lastname: Prabpai
authors.forename: Manat
authors.initials: M
authors.lastname: Pohmakotr