Please use this identifier to cite or link to this item:
https://hdl.handle.net/1959.11/8140
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: | The Journal of Organic Chemistry, 73(7), p. 2633-2640 | Publisher: | American Chemical Society | Place of Publication: | United States of America | ISSN: | 1520-6904 0022-3263 |
Fields of Research (FoR) 2008: | 030503 Organic Chemical Synthesis | Socio-Economic Objective (SEO) 2008: | 970103 Expanding Knowledge in the Chemical Sciences | Peer Reviewed: | Yes | HERDC Category Description: | C1 Refereed Article in a Scholarly Journal |
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Appears in Collections: | Journal Article |
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