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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) ; Pederson, Daniel Sejer (author); Taylor, Dennis K (author); Tiekink, Edward R T (author)||Publication Date:||2008||DOI:||10.1021/jo7024256||Handle Link:||https://hdl.handle.net/1959.11/8140||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||Statistics to Oct 2018:||Visitors: 229
|Appears in Collections:||Journal Article|
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