Highly Enantioselective Synthesis of (2S)-α-(Hydroxymethyl)-glutamic Acid by the Catalytic Michael Addition of 2-Naphthalen-1-yl-2-oxazoline-4-carboxylic Acid tert -Butyl Ester

Highly enantioselective synthesis of a potent metabotropic receptor ligand, (2S)-α-(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 CH2Cl2 at −60 °...

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Published inOrganic letters Vol. 7; no. 15; pp. 3207 - 3209
Main Authors Lee, Yeon-Ju, Lee, Jihye, Kim, Mi-Jeong, Jeong, Byeong-Seon, Lee, Jeong-Hee, Kim, Taek-Soo, Lee, Jihoon, Ku, Jin-Mo, Jew, Sang-sup, Park, Hyeung-geun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.07.2005
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Combinatorial Chemistry Techniques
Glutamates - chemical synthesis
Ligands
Molecular Structure
Naphthalenes - chemistry
Oxazoles - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
GLUTAMATE RECEPTORS
POTENT
DESIGN
SOLID-PHASE SYNTHESIS
PHARMACOLOGICAL CHARACTERIZATION
ALKYLATION
DERIVATIVES
ACCESS
AGONIST
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Summary:Highly enantioselective synthesis of a potent metabotropic receptor ligand, (2S)-α-(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 CH2Cl2 at −60 °C in the presence of (S)-binaphthyl quaternary ammonium salt 4.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol050920s