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https://hdl.handle.net/1959.11/16535| Title: | Nucleophilic Trapping of Alkoxy-Stabilized Oxyallyl Systems Generated from Inosose 2-O-Mesylates | Contributor(s): | Stockton, Kieran (author); Glover, Stephen (author) ; Greatrex, Ben (author) |
Publication Date: | 2015 | Open Access: | Yes | DOI: | 10.1055/s-0034-1379490 |
Handle Link: | https://hdl.handle.net/1959.11/16535 | Abstract: | Protected inosose 2-O-mesylates generate oxyallyl systems by elimination of the mesylate group after enolization. The reaction is promoted by weak bases such as triethylamine and azide, and the oxyallyl systems are then trapped by nucleophilic alcohols or azide. Computations using DFT/B3LYP confirm that the singlet planar oxyallyl is stabilized by the exocyclic alkoxy group. | Publication Type: | Journal Article | Source of Publication: | Synlett, 26(1), p. 111-115 | Publisher: | Georg Thieme Verlag | Place of Publication: | Germany | ISSN: | 1437-2096 0936-5214 |
Fields of Research (FoR) 2008: | 030503 Organic Chemical Synthesis 030502 Natural Products Chemistry 030505 Physical Organic Chemistry |
Fields of Research (FoR) 2020: | 340503 Organic chemical synthesis 340505 Physical organic chemistry 340502 Natural products and bioactive compounds |
Socio-Economic Objective (SEO) 2008: | 970103 Expanding Knowledge in the Chemical Sciences 860803 Human Pharmaceutical Treatments (e.g. Antibiotics) |
Socio-Economic Objective (SEO) 2020: | 280105 Expanding knowledge in the chemical sciences 240803 Human pharmaceutical treatments |
Peer Reviewed: | Yes | HERDC Category Description: | C1 Refereed Article in a Scholarly Journal |
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| Appears in Collections: | Journal Article School of Rural Medicine School of Science and Technology |
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