title: Preparation of 3-sulfonylated 3,3-disubstituted oxindoles by the addition of sulfinate salts to 3-halooxindoles.
abstract: An efficient method for the preparation of 3-sulfonylated 3,3-disubstituted oxindole derivatives has been developed. The protocol involves a base-catalyzed addition of sulfinate salts to 3-halooxindoles, affording a wide range of 3-sulfonylated 3,3-disubstituted oxindoles in good to excellent yields under mild conditions. A preliminary trial of asymmetric catalytic version was conducted and gave promising enantioselectivity. The mechanism for the reaction was tentatively explored with the help of mass spectrometric analysis.
authors.affiliation: †National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.|§University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Jian
authors.initials: J
authors.lastname: Zuo
authors.affiliation: ‡Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Zhi-Jun
authors.initials: ZJ
authors.lastname: Wu
authors.affiliation: †National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.|§University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Jian-Qiang
authors.initials: JQ
authors.lastname: Zhao
authors.affiliation: †National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.|§University of Chinese Academy of Sciences, Beijing 100049, China.
authors.forename: Ming-Qiang
authors.initials: MQ
authors.lastname: Zhou
authors.forename: Xiao-Ying
authors.initials: XY
authors.lastname: Xu
authors.affiliation: †National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Xiao-Mei
authors.initials: XM
authors.lastname: Zhang
authors.affiliation: †National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Wei-Cheng
authors.initials: WC
authors.lastname: Yuan
mesh_terms: D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D012492:Salts / Q000737:chemistry; D013441:Sulfinic Acids / Q000737:chemistry*
chemical_list: D006846:Hydrocarbons, Halogenated; D007211:Indoles; D000078183:Oxindoles; D012492:Salts; D013441:Sulfinic Acids; C022960:2-oxindole