title: Catalytic asymmetric construction of quaternary α-amino acid containing pyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylates.
abstract: The first catalytic enantioselective 1,3-dipolar cycloaddition of azomethine ylides to α-aminoacrylate catalyzed by a AgOAc/ferrocenyl oxazolinylphosphine (FOXAP) system was developed, which exhibits excellent exo- and enantioselectivity (92-99 % ee). This process provides efficient access to useful 4-aminopyrrolidine-2,4-dicarboxylic acid (APDC)-like compounds containing a unique quaternary α-amino acid unit.
authors.affiliation: Shanghai Key Laboratory of New Drug Design and School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, PR China.
authors.forename: Zheng
authors.initials: Z
authors.lastname: Wang
authors.forename: Shuai
authors.initials: S
authors.lastname: Luo
authors.forename: Shoude
authors.initials: S
authors.lastname: Zhang
authors.forename: Wu-Lin
authors.initials: WL
authors.lastname: Yang
authors.forename: Yang-Zi
authors.initials: YZ
authors.lastname: Liu
authors.forename: Honglin
authors.initials: H
authors.lastname: Li
authors.forename: Xiaoyan
authors.initials: X
authors.lastname: Luo
authors.forename: Wei-Ping
authors.initials: WP
authors.lastname: Deng
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D003998:Dicarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D001391:Azo Compounds; D003998:Dicarboxylic Acids; D011759:Pyrrolidines; D013882:Thiosemicarbazones; C512188:azomethine; C015102:dehydroalanine; D000409:Alanine