title: Enantioselective synthesis of β-amino acid derivatives via nickel-promoted regioselective carboxylation of ynamides and rhodium-catalyzed asymmetric hydrogenation.
abstract: We succeeded in the development of a new method for enantioselective synthesis of α-substituted-β-amino acid derivatives. Thus, nickel(0)-promoted carboxylation of ynamide gave the α-substituted-β-aminoacrylate derivative in a highly regioselective manner. Then, rhodium-catalyzed asymmetric hydrogenation of the α-substituted β-aminoacrylate produced the corresponding α-substituted β-amino acid derivative as an optically active form.
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. biyo@pharm.hokudai.ac.jp.
authors.forename: Nozomi
authors.initials: N
authors.lastname: Saito
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. biyo@pharm.hokudai.ac.jp.
authors.forename: Iman
authors.initials: I
authors.lastname: Abdullah
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. biyo@pharm.hokudai.ac.jp.
authors.forename: Kayoko
authors.initials: K
authors.lastname: Hayashi
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. biyo@pharm.hokudai.ac.jp.
authors.forename: Katsuyuki
authors.initials: K
authors.lastname: Hamada
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. biyo@pharm.hokudai.ac.jp.
authors.forename: Momoko
authors.initials: M
authors.lastname: Koyama
authors.affiliation: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan. biyo@pharm.hokudai.ac.jp.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Sato
mesh_terms: D000577:Amides / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D006865:Hydrogenation; D009532:Nickel / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000596:Amino Acids; D002264:Carboxylic Acids; D009532:Nickel; D012238:Rhodium