Catalytic asymmetric synthesis of glutamate analogues.
Utilizing our lateral metalation coupled with Jacobsen's catalytic asymmetric amino nitrile synthesis, we have demonstrated the ability to synthesize isoxazole-containing amino acid glutamate analogues in high yield and high enantiomeric excesses. Chiral centers alpha or beta at the C-5 position do not detract from diastereoselectivity of the Jacobsen-Strecker reaction. [reaction: see text]
Burkhart
David J
DJ
Department of Chemistry, University of Idaho, 301 Renfrew Hall, Moscow, ID 83844-2343, USA.
McKenzie
Andrew R
AR
Nelson
Jared K
JK
Myers
Katherine I
KI
Zhao
Xue
X
Magnusson
Kathy R
KR
Natale
Nicholas R
NR
D000818:Animals; D001667:Binding, Competitive; D001921:Brain / Q000378:metabolism; D002384:Catalysis; D005971:Glutamates / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D007555:Isoxazoles / Q000737:chemistry; D051379:Mice; D008956:Models, Chemical; D009474:Neurons / Q000187:drug effects*; D018377:Neurotransmitter Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D013237:Stereoisomerism; D013696:Temperature
D005971:Glutamates; D007555:Isoxazoles; D018377:Neurotransmitter Agents