title: Organocatalytic highly enantioselective monofluoroalkylation of 3-bromooxindoles: construction of fluorinated 3,3'-disubstituted oxindoles and their derivatives.
abstract: A new practical organocatalytic asymmetric protocol for the introduction of a monofluoroalkyl group into the oxindole framework has been successfully developed. Excellent diastereoselectivities (>20:1 dr) and enantioselectivities (93-99% ee) of the products were obtained with a wide range of pre-electrophiles (3-bromooxindoles) and prenucleophiles (α-fluorinated β-keto gem-diols). The obtained products themselves and their derivatives may significantly benefit drug discovery.
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University , Lanzhou 730000, P.R. China.
authors.forename: Chongyang
authors.initials: C
authors.lastname: Wu
authors.forename: Guofeng
authors.initials: G
authors.lastname: Li
authors.forename: Wangsheng
authors.initials: W
authors.lastname: Sun
authors.forename: Ming
authors.initials: M
authors.lastname: Zhang
authors.forename: Liang
authors.initials: L
authors.lastname: Hong
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole