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https://hdl.handle.net/1959.11/29369
Title: | Aziridination and aza-Wharton Reactions of Levoglucosenone | Contributor(s): | Ledingham, Edward T (author); Greatrex, Ben W (author)![]() |
Publication Date: | 2019-02-06 | DOI: | 10.1071/CH18574 | Handle Link: | https://hdl.handle.net/1959.11/29369 | Abstract: | Efficient conditions have been developed for the diastereoselective aziridination of the biomass pyrolysis product (−)-levoglucosenone, via the reaction of primary aliphatic amines with 3-iodolevoglucosenone. In contrast to the reactions of aliphatic amines, the use of 4-methoxyaniline resulted in an aza-Michael-initiated dimerisation reaction, and 1,3-diphenylurea gave a 2-imidazolidinone. The aziridine products were transformed using the aza-Wharton reaction, affording novel sulfonamide and amine-substituted 6,8-dioxabicyclo[3.2.1]oct-3-enes with potential as sp3-rich chiral scaffolds. | Publication Type: | Journal Article | Source of Publication: | Australian Journal of Chemistry, 72(5), p. 362-368 | Publisher: | CSIRO Publishing | Place of Publication: | Australia | ISSN: | 1445-0038 0004-9425 |
Fields of Research (FoR) 2008: | 030503 Organic Chemical Synthesis | Fields of Research (FoR) 2020: | 340503 Organic chemical synthesis | Socio-Economic Objective (SEO) 2008: | 970103 Expanding Knowledge in the Chemical Sciences | Socio-Economic Objective (SEO) 2020: | 280105 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 School of Rural Medicine School of Science and Technology |
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