title: Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles].
abstract: An efficient and unprecedented organocatalytic asymmetric reaction of 3-pyrrolyl-oxindoles with α,β-unsaturated aldehydes to generate spirocyclic oxindole compounds was developed. The reactions were catalyzed by diphenylprolinol silyl ether and 2-fluorobenzoic acid via an asymmetric Michael/Friedel-Crafts cascade process, followed by dehydration with p-toluenesulfonic acid to afford a wide variety of structurally diverse spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindole] derivatives in high yields (up to 93%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 97% ee).
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 10049, China.
authors.forename: Yong
authors.initials: Y
authors.lastname: You
authors.affiliation: ‡School of Pharmacy, Zunyi Medical University, Zunyi 563000, China.
authors.forename: Bao-Dong
authors.initials: BD
authors.lastname: Cui
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 10049, China.
authors.forename: Ming-Qiang
authors.initials: MQ
authors.lastname: Zhou
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 10049, China.
authors.forename: Jian
authors.initials: J
authors.lastname: Zuo
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 10049, 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.
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: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000078183:Oxindoles; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007211:Indoles; D000078183:Oxindoles; D011758:Pyrroles; D013141:Spiro Compounds; C022960:2-oxindole