title: Organocatalytic asymmetric Michael addition of 3-substituted oxindoles to α,β-unsaturated acyl phosphonates for the synthesis of 3,3'-disubstituted oxindoles with chiral squaramides.
abstract: A highly enantioselective Michael addition of 3-monosubstituted oxindoles to α,β-unsaturated acyl phosphonates with chiral squaramides as catalysts is investigated for the first time. A wide range of 3,3'-disubstituted oxindole adducts bearing adjacent quaternary and tertiary stereogenic centres could be smoothly obtained in good yields (up to 98%), diastereo- (up to >99 : 1 dr) and enantioselectivities (up to 98% ee) with the developed protocols.
authors.affiliation: National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China. yuanwc@cioc.ac.cn xuxy@cioc.ac.cn.
authors.forename: Lin
authors.initials: L
authors.lastname: Chen
authors.forename: Yong
authors.initials: Y
authors.lastname: You
authors.forename: Ming-Liang
authors.initials: ML
authors.lastname: Zhang
authors.forename: Jian-qiang
authors.initials: JQ
authors.lastname: Zhao
authors.forename: Jian
authors.initials: J
authors.lastname: Zuo
authors.forename: Xiao-Mei
authors.initials: XM
authors.lastname: Zhang
authors.forename: Wei-Cheng
authors.initials: WC
authors.lastname: Yuan
authors.forename: Xiao-Ying
authors.initials: XY
authors.lastname: Xu
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D000577:Amides; D007211:Indoles; D063065:Organophosphonates; D000078183:Oxindoles; C022960:2-oxindole