title: Highly enantioselective fluorination of unprotected 3-substituted oxindoles: one-step synthesis of BMS 204352 (MaxiPost).
abstract: The catalytic enantioselective fluorination of N-H-free 3-substituted oxindoles was accomplished by a Sc(III)/N,N'-dioxide complex. Under mild reaction conditions, a series of 3-aryl- and 3-alkyl-3-fluoro-2-oxindoles were obtained in excellent yields (up to 98%) and enantioselectivities (up to 99% ee) by using N-fluorobisbenzenesulfonimide (NFSI) as the fluorination agent. MaxiPost was synthesized efficiently in 81% yield with 96% ee.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.forename: Yunfei
authors.initials: Y
authors.lastname: Cai
authors.forename: Weiliang
authors.initials: W
authors.lastname: Chen
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: C424388:BMS204352; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole