title: Asymmetric Michael addition of α-substituted isocyanoacetates with maleimides catalyzed by chiral tertiary amine thiourea.
abstract: A highly diastereoselective and enantioselective Michael addition of α-substituted isocyanoacetates with maleimides catalyzed by bifunctional tertiary amine thioureas has been developed. Various chiral succinimide derivatives bearing adjacent quaternary and tertiary stereocenters were prepared in excellent yields (up to 98%), diastereoselectivities (up to 99:1), and enantioselectivities (up to 98% ee). The synthetic utility of chiral succinimide derivatives is also demonstrated in the preparation of h5-HT(1d) receptor agonist motifs.
authors.affiliation: Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
authors.forename: Jian-Fei
authors.initials: JF
authors.lastname: Bai
authors.forename: Liang-Liang
authors.initials: LL
authors.lastname: Wang
authors.forename: Lin
authors.initials: L
authors.lastname: Peng
authors.forename: Yun-Long
authors.initials: YL
authors.lastname: Guo
authors.forename: Li-Na
authors.initials: LN
authors.lastname: Jia
authors.forename: Fang
authors.initials: F
authors.lastname: Tian
authors.forename: Guang-Yun
authors.initials: GY
authors.lastname: He
authors.forename: Xiao-Ying
authors.initials: XY
authors.lastname: Xu
authors.forename: Li-Xin
authors.initials: LX
authors.lastname: Wang
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D017953:Isocyanates / Q000737:chemistry*; D008301:Maleimides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
chemical_list: D000085:Acetates; D000588:Amines; D017953:Isocyanates; D008301:Maleimides; D013890:Thiourea