title: Chiral N-Phosphonyl Imines for an Aza-Morita-Baylis-Hillman Reaction via Group-Assisted Purification (GAP) Chemistry.
abstract: Seventeen examples of aza-Morita-Baylis-Hillman (aza-MBH) adducts have been synthesized by reacting chiral N-phosphonyl imines with acrylonitrile in good to excellent yields (up to 96%) and high diastereoselectivity (up to 99:1 dr). The synthesis of these adducts followed the method of group-assisted purification (GAP) chemistry, in which the pure aza-MBH products were readily obtained by washing the crude products with cosolvents of hexane and ethyl acetate.
authors.affiliation: Institute of Chemistry and Biomedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University , Nanjing, 210093 China.
authors.forename: Bing
authors.initials: B
authors.lastname: Yang
authors.affiliation: Institute of Chemistry and Biomedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University , Nanjing, 210093 China.
authors.forename: Minxing
authors.initials: M
authors.lastname: Shen
authors.affiliation: Institute of Chemistry and Biomedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University , Nanjing, 210093 China.
authors.forename: Xiaozhou
authors.initials: X
authors.lastname: Ji
authors.affiliation: Institute of Chemistry and Biomedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University , Nanjing, 210093 China.
authors.forename: Ziyan
authors.initials: Z
authors.lastname: Xu
authors.affiliation: Institute of Chemistry and Biomedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University , Nanjing, 210093 China.
authors.forename: Hao
authors.initials: H
authors.lastname: Sun
authors.affiliation: Department of Chemistry and Biochemistry, Texas Tech University , Lubbock, Texas 79409-1061, United States.
authors.forename: Bo
authors.initials: B
authors.lastname: Jiang
authors.affiliation: Institute of Chemistry and Biomedical Sciences and School of Chemistry and Chemical Engineering, Nanjing University , Nanjing, 210093 China.
authors.forename: Guigen
authors.initials: G
authors.lastname: Li
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000181:Acrylonitrile / Q000737:chemistry*; D002384:Catalysis; D006586:Hexanes / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D006586:Hexanes; D007097:Imines; C026385:n-hexane; C007650:ethyl acetate; D000181:Acrylonitrile