Catalytic asymmetric synthesis of glutamate analogues.

TitleCatalytic asymmetric synthesis of glutamate analogues.
Publication TypeJournal Article
Year of Publication2004
AuthorsBurkhart DJ, McKenzie AR, Nelson JK, Myers KI, Zhao X, Magnusson KR, Natale NR
JournalOrganic letters
Volume6
Issue8
Pagination1285-8
Date Published2004 Apr 15
ISSN1523-7060
KeywordsAnimals, Binding, Competitive, Brain, Catalysis, Glutamates, Isoxazoles, Mice, Models, Chemical, Neurons, Neurotransmitter Agents, Stereoisomerism, Temperature
Abstract

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]

DOI10.1021/ol049619m
Alternate JournalOrg. Lett.