title: Highly enantioselective synthesis of (2S)-alpha-(hydroxymethyl)-glutamic acid by the catalytic Michael addition of 2-naphthalen-1-yl-2-oxazoline-4-carboxylic acid tert-butyl ester.
abstract: [reaction: see text]. Highly enantioselective synthesis of a potent metabotropic receptor ligand, (2S)-alpha-(hydroxymethyl)-glutamic acid (2, HMG) was accomplished by the catalytic Michael addition of 2-naphthalen-1-yl-2-oxazoline-4-carboxylic acid tert-butyl ester (3b), using the phosphazene base, BEMP, in CH(2)Cl(2) at -60 degrees C in the presence of (S)-binaphthyl quaternary ammonium salt 4.
authors: Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, Korea.
authors: Yeon-Ju
authors: YJ
authors: Lee
authors: Jihye
authors: J
authors: Lee
authors: Mi-Jeong
authors: MJ
authors: Kim
authors: Byeong-Seon
authors: BS
authors: Jeong
authors: Jeong-Hee
authors: JH
authors: Lee
authors: Taek-Soo
authors: TS
authors: Kim
authors: Jihoon
authors: J
authors: Lee
authors: Jin-Mo
authors: JM
authors: Ku
authors: Sang-sup
authors: SS
authors: Jew
authors: Hyeung-geun
authors: HG
authors: Park
mesh_terms: D020650:Combinatorial Chemistry Techniques; D005971:Glutamates / Q000138:chemical synthesis*; D008024:Ligands; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C449086:(hydroxymethyl)glutamic acid; C509884:2-naphthalen-1-yl-2-oxazoline-4-carboxylic acid tert-butyl ester; D005971:Glutamates; D008024:Ligands; D009281:Naphthalenes; D010080:Oxazoles