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.
[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.
Lee
Yeon-Ju
YJ
Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, Korea.
Lee
Jihye
J
Kim
Mi-Jeong
MJ
Jeong
Byeong-Seon
BS
Lee
Jeong-Hee
JH
Kim
Taek-Soo
TS
Lee
Jihoon
J
Ku
Jin-Mo
JM
Jew
Sang-sup
SS
Park
Hyeung-geun
HG
D020650:Combinatorial Chemistry Techniques; D005971:Glutamates / Q000138:chemical synthesis*; D008024:Ligands; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D013237:Stereoisomerism
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