title: Enantioselective Synthesis of 3,3-Disubstituted Oxindoles Bearing Two Different Heteroatoms at the C3 Position by Organocatalyzed Sulfenylation and Selenenylation of 3-Pyrrolyl-oxindoles.
abstract: Catalytic asymmetric sulfenylation and selenenylation of 3-pyrrolyl-oxindoles for the synthesis of 3,3-disubstituted oxindoles bearing two different heteroatoms at the C3 position have been achieved with commercially available cinchonidine as catalyst. A wide range of optically active 3-thio-3-pyrrolyl-oxindoles and 3-seleno-3-pyrrolyl-oxindoles could be smoothly obtained under mild conditions with satisfactory results. The promising applicability of the protocol was also demonstrated by large-scale production.
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: Yong
authors.initials: Y
authors.lastname: You
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: Zhen-Hua
authors.initials: ZH
authors.lastname: Wang
authors.affiliation: †National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
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: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D018036:Selenium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D002930:Cinchona Alkaloids; D006571:Heterocyclic Compounds; D007211:Indoles; D000078183:Oxindoles; D011758:Pyrroles; D018036:Selenium Compounds; D013438:Sulfhydryl Compounds; C022960:2-oxindole; C041622:cinchonidine