title: Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base.
abstract: Asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid (vinyl-ACCA) is in extremely high demand due to the pharmaceutical importance of this tailor-made, sterically constrained α-amino acid. Here we report the development of an advanced procedure for preparation of the target amino acid via two-step SN2 and SN2' alkylation of novel axially chiral nucleophilic glycine equivalent. Excellent yields and diastereoselectivity coupled with reliable and easy scalability render this method of immediate use for practical synthesis of (1R,2S)-vinyl-ACCA.
authors.affiliation: Hamari Chemicals Ltd, 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan.
authors.forename: Aki
authors.initials: A
authors.lastname: Kawashima
authors.affiliation: Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai, 201203, China.
authors.forename: Shuangjie
authors.initials: S
authors.lastname: Shu
authors.affiliation: Hamari Chemicals Ltd, 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan.
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Takeda
authors.affiliation: Hamari Chemicals Ltd, 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan.
authors.forename: Akie
authors.initials: A
authors.lastname: Kawamura
authors.affiliation: Hamari Chemicals Ltd, 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan.
authors.forename: Tatsunori
authors.initials: T
authors.lastname: Sato
authors.affiliation: Hamari Chemicals Ltd, 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan.
authors.forename: Hiroki
authors.initials: H
authors.lastname: Moriwaki
authors.affiliation: Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai, 201203, China.
authors.forename: Jiang
authors.initials: J
authors.lastname: Wang
authors.affiliation: Hamari Chemicals Ltd, 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan.
authors.forename: Kunisuke
authors.initials: K
authors.lastname: Izawa
authors.affiliation: Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain.
authors.forename: José Luis
authors.initials: JL
authors.lastname: Aceña
authors.affiliation: Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain. vadym.soloshonok@ehu.es.|IKERBASQUE, Basque Foundation for Science, Maria Diaz de Haro 3, 48013, Bilbao, Spain. vadym.soloshonok@ehu.es.
authors.forename: Vadim A
authors.initials: VA
authors.lastname: Soloshonok
authors.affiliation: Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai, 201203, China.
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D000478:Alkylation; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002384:Catalysis; D002413:Cations, Divalent; D056831:Coordination Complexes / Q000138:chemical synthesis*; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis*; D005998:Glycine / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D012545:Schiff Bases / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis*
chemical_list: C587841:(1R,2S)-1-amino- 2-vinylcyclopropanecarboxylic acid; D000998:Antiviral Agents; D002413:Cations, Divalent; D056831:Coordination Complexes; D003521:Cyclopropanes; D012545:Schiff Bases; D014753:Vinyl Compounds; D009532:Nickel; D005998:Glycine
keywords: Amino acids; Anti-viral (HCV) activity; Asymmetric synthesis; Chirality; Schiff bases