Aziridination and aza-Wharton Reactions of Levoglucosenone

Edward T. Ledingham; Ben W. Greatrex

doi:10.1071/CH18574

RESEARCH ARTICLE

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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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Aziridination and aza-Wharton Reactions of Levoglucosenone

Abstract

References

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