Please use this identifier to cite or link to this item: 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)orcid 
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
Appears in Collections:Journal Article
School of Rural Medicine
School of Science and Technology

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