title: Enantioselective synthesis of 3-fluoro-3-allyl-oxindoles via phosphine-catalyzed asymmetric γ-addition of 3-fluoro-oxindoles to 2,3-butadienoates.
abstract: The first phosphine-catalyzed enantioselective γ-addition of 3-fluoro-oxindoles to 2,3-butadienoates has been developed. A range of 3-fluoro-substituted oxindole substrates were employed, and oxindoles containing a 3-fluoro quaternary center were constructed in high yields and with excellent enantioselectivities. The γ-addition products could be converted readily to optically enriched 3-fluoro-3-allyl oxindole derivatives.
authors.affiliation: Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543, Republic of Singapore. chmlyx@nus.edu.sg.
authors.forename: Tianli
authors.initials: T
authors.lastname: Wang
authors.forename: Ding Long
authors.initials: DL
authors.lastname: Hoon
authors.forename: Yixin
authors.initials: Y
authors.lastname: Lu
mesh_terms: D002070:Butadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D005720:Gamma Rays; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D000078183:Oxindoles; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002070:Butadienes; D007211:Indoles; D000078183:Oxindoles; D010720:Phosphines; C022960:2-oxindole; C044646:phosphine; C031763:1,3-butadiene