title: Catalytic, asymmetric Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives. Efficient synthesis of a novel inhibitor of ceramide trafficking, HPA-12.
abstract: [reaction: see text] Catalytic, enantioselective Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives are described. A chiral copper catalyst prepared from Cu(OTf)(2) and a chiral diamine ligand is used. A novel inhibitor of ceramide trafficking, HPA-12, is efficiently synthesized using this reaction.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, CREST, Japan Science and Technology Corporation, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. skobayas@mol.f.u-tokyo.ac.jp
authors.forename: Shū
authors.initials: S
authors.lastname: Kobayashi
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Matsubara
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Kitagawa
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D002518:Ceramides / Q000037:antagonists & inhibitors*; D004952:Esters; D007098:Imino Acids / Q000737:chemistry*; D008968:Molecular Conformation; D013107:Sphingolipids / Q000037:antagonists & inhibitors; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000596:Amino Acids; D002518:Ceramides; D004952:Esters; D007098:Imino Acids; C441643:N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide; D013107:Sphingolipids