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RESEARCH ARTICLE
Contents Vol 72(5)

Aziridination and aza-Wharton Reactions of Levoglucosenone

Edward T. Ledingham A and Ben W. Greatrex A B C
+ Author Affiliations
- Author Affiliations

A School of Science and Technology, University of New England, Armidale, NSW 2351, Australia.

B School of Rural Medicine, University of New England, Armidale, NSW 2351, Australia.

C Corresponding author. Email: ben.greatrex@une.edu.au

Australian Journal of Chemistry 72(5) 362-368 https://doi.org/10.1071/CH18574
Submitted: 19 November 2018  Accepted: 8 January 2019   Published: 6 February 2019

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.


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