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RESEARCH ARTICLE
Contents Vol 74(9)

The Synthesis, Structural Characterisation, and Chemoselective Manipulation of Certain Functionalised Cyclic Sulfates Derived from Chiral, Non-Racemic, and Polysubstituted Bicyclo[2.2.2]octane-2,3-diols

Martin G. Banwell https://orcid.org/0000-0002-0582-475X A B C , Antony L. Crisp https://orcid.org/0000-0001-7173-4376 B , BoRa Lee B , Ping Lan https://orcid.org/0000-0002-9285-3259 A , Hannah E. Bollard B , Jas S. Ward B and Anthony C. Willis B
+ Author Affiliations
- Author Affiliations

A Institute for Advanced and Applied Chemical Synthesis, Jinan University, Guangzhou, 510632, China.

B Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.

C Corresponding author. Email: mgb@rsc.anu.edu.au

Australian Journal of Chemistry 74(9) 640-651 https://doi.org/10.1071/CH21140
Submitted: 15 June 2021  Accepted: 7 July 2021   Published: 28 July 2021

Abstract

Certain cyclic sulfates (e.g. 23) together with various of their precursor sulfites (e.g. 21 and 22) have been prepared from the corresponding chiral, non-racemic bicyclo[2.2.2]octane-2,3-diols (e.g. 20). Such diols are obtained by engaging the corresponding enzymatically derived and enantiomerically enriched or homochiral cis-1,2-dihydrocatechol (e.g. 10) or certain derivatives in either inter- or intra-molecular Diels–Alder cycloaddition reactions. Other functionalities present within the title compounds can be chemoselectively manipulated without adversely affecting the associated sulfate residues.

Keywords: cis-1,2-dihydrocatechol, cyclic sulfate, cyclic sulfite, Diels–Alder cycloaddition, heterocycle, oxidation, reduction, X-ray crystal structure.


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