title: An Organocatalytic Asymmetric Friedel-Crafts Addition/Fluorination Sequence: Construction of Oxindole-Pyrazolone Conjugates Bearing Vicinal Tetrasubstituted Stereocenters.
abstract: A highly efficient and practical one-pot sequential process, consisting of an organocatalytic enantioselective Friedel-Crafts-type addition of 4-nonsubstituted pyrazolones to isatin-derived N-Boc ketimines and a subsequent diastereoselective fluorination of the pyrazolone moiety, is developed. This reaction sequence delivers novel oxindole-pyrazolone adducts featuring vicinal tetrasubstituted stereocenters with a 0.5 mol % catalyst loading in high yield with excellent enantio- and diastereocontrol. Notably, chloro, bromo, and thioether functionalities can be readily incorporated, rendering a broad diversity of the product.
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Xiaoze
authors.initials: X
authors.lastname: Bao
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Baomin
authors.initials: B
authors.lastname: Wang
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Longchen
authors.initials: L
authors.lastname: Cui
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Guodong
authors.initials: G
authors.lastname: Zhu
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Yuli
authors.initials: Y
authors.lastname: He
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Jingping
authors.initials: J
authors.lastname: Qu
authors.affiliation: State Key Laboratory of Fine Chemicals, School of Pharmaceutical Science and Technology, Dalian University of Technology , Dalian 116024, P. R. China.
authors.forename: Yuming
authors.initials: Y
authors.lastname: Song