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Title: A Concise Route to β-Cyclopropyl Amino Acids Utilizing 1,2-Dioxines and Stabilized Phosphonate Nucleophiles
Contributor(s): Avery, Thomas D (author); Greatrex, Ben  (author)orcid ; Pederson, Daniel Sejer (author); Taylor, Dennis K (author); Tiekink, Edward R T (author)
Publication Date: 2008
DOI: 10.1021/jo7024256
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Abstract: 1,2-Dioxines react with glycine-derived phosphonate nucleophiles via a multistep cascade reaction to give β-cyclopropyl amino acid derivatives in good yield with excellent control of the cyclopropane stereocentres. The cyclopropyl ketones were oxidized to the corresponding carboxylic esters using Baeyer−Villiger conditions. Standard deprotection protocols produced a series of known β-cyclopropyl amino acids that are selective and potent agonists or antagonists of the metabotropic glutamate receptors in excellent yields.
Publication Type: Journal Article
Source of Publication: Journal of Organic Chemistry, 73(7), p. 2633-2640
Publisher: American Chemical Society
Place of Publication: United States of America
ISSN: 1520-6904
Field of Research (FOR): 030503 Organic Chemical Synthesis
Socio-Economic Outcome Codes: 970103 Expanding Knowledge in the Chemical Sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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