Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH21140
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.


References

[1]  (a) See for example: C. Mushti, M. I. Papisov, Molecules 2012, 17, 13266.
         | Crossref | GoogleScholarGoogle Scholar | 23135631PubMed |
      (b) M. Artola, L. Wu, M. J. Ferraz, C.-L. Kuo, L. Raich, I. Z. Breen, W. A. Offen, J. D. C. Codée, G. A. van der Marel, C. Rovira, J. M. F. G. Aerts, G. J. Davies, H. S. Overkleeft, ACS Cent. Sci. 2017, 3, 784.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  (a) For some key and representative publications see: Y. Gao, K. B. Shaprless, J. Am. Chem. Soc. 1988, 110, 7538.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) M. S. Berridge, M. P. Franceschini, E. Rosenfeld, T. J. Tewson, J. Org. Chem. 1990, 55, 1211.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) J. G. Steinmann, J. H. Phillips, W. J. Sanders, L. L. Kiessling, Org. Lett. 2001, 3, 3557.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) N. Takechi, S. Ait-Mohand, M. Medebielle, W. R. Dolbier, Org. Lett. 2002, 4, 4671.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) M. Inoue, S. Motomatsu, M. Nakada, Synth. Commun. 2003, 33, 2857.
         | Crossref | GoogleScholarGoogle Scholar |
      (f) R. Tello-Aburto, T. D. Newar, W. A. Maio, J. Org. Chem. 2012, 77, 6271.
         | Crossref | GoogleScholarGoogle Scholar |
      (g) D. R. Boyd, N. D. Sharma, M. Kaik, P. B. A. McIntyre, J. F. Malone, P. J. Stevenson, Org. Biomol. Chem. 2014, 12, 2128.
         | Crossref | GoogleScholarGoogle Scholar |
      (h) A. Jakubowska, G. Zuchowski, K. Kulig, Tetrahedron Asymmetry 2015, 26, 1261.
         | Crossref | GoogleScholarGoogle Scholar |
      (i) M. S. Eno, A. Lu, J. P. Morken, J. Am. Chem. Soc. 2016, 138, 7824.
         | Crossref | GoogleScholarGoogle Scholar |
      (j) V. Laserna, E. Martin, E. C. Escudero-Adán, A. W. Kleij, Adv. Synth. Catal. 2016, 358, 3832.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) For key reviews of this topic see: B. B. Lohray, Synthesis 1992, 1035.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) H.-S. Byun, L. He, R. Bittmann, Tetrahedron 2000, 56, 7051.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  M. K. Sharma, M. G. Banwell, A. C. Willis, Asian J. Org. Chem. 2014, 3, 632.
         | Crossref | GoogleScholarGoogle Scholar |

[5]     (a) For recent reviews on the microbial production and the chemical utilisation of cis-1,2-dihydrocatechols see: S. E. Lewis, in Asymmetric Desymmetrization Reactions (Ed. S.-L. You) 2016 pp. 279–346 (Wiley VCH: Weinheim).
      (b) T. Hudlicky, ACS Omega 2018, 3, 17326.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) P. Lan, S. Ye, M. G. Banwell, Chem. Asian J. 2019, 14, 4001.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  M. G. Banwell, J. R. Dupuche, R. W. Gable, Aust. J. Chem. 1996, 49, 639.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  T. A. Reekie, K. A. B. Austin, M. G. Banwell, A. C. Willis, Aust. J. Chem. 2008, 61, 94.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  S. G. Stewart, G. J. Harfoot, K. J. McRae, Y. Teng, L.-J. Yu, B. Chen, R. Cammi, M. L. Coote, M. G. Banwell, A. C. Willis, J. Org. Chem. 2020, 85, 13080.
         | Crossref | GoogleScholarGoogle Scholar | 32914974PubMed |

[9]  F. Tang, P. Lan, B. Bolte, M. G. Banwell, J. S. Ward, A. C. Willis, J. Org. Chem. 2018, 83, 14049.
         | Crossref | GoogleScholarGoogle Scholar | 30359031PubMed |

[10]  (a) For examples of related processes see: K. A. B. Austin, M. G. Banwell, A. C. Willis, Org. Lett. 2008, 10, 4465.
         | Crossref | GoogleScholarGoogle Scholar |
      (b) E.-L. Chang, B. D. Schwartz, A. G. Draffan, M. G. Banwell, A. C. Willis, Chem. Asian J. 2015, 10, 427.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) R. N. Muhammad, A. G. Draffan, M. G. Banwell, A. C. Willis, Synlett 2016, 27, 61.
      (d) R. N. Muhammad, E. L. Chang, A. G. Draffan, A. C. Willis, P. D. Carr, M. G. Banwell, Aust. J. Chem. 2018, 71, 655.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923.
         | Crossref | GoogleScholarGoogle Scholar |

[12]  A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  DENZO–SMN: Z. Otwinowski, W. Minor, in Methods in Enzymology, Volume 276: Macromolecular Crystallography, Part A (Eds C. W. Carter Jr, R. M. Sweet) 1997, pp. 307–326 (Academic Press: New York, NY).

[14]  CrysAlisPro PRO, version 1.171.37.35h 2015 (release 2 Sep 2015 CrysAlis171.NET) (compiled 9 Feb 2015, 16:26:32) (Agilent Technologies: Oxfordshire, UK).

[15]  SIR92: A Altomare, G Cascarano, C Giacovazzo, A Guagliardi, M. C. Burla, G Polidori, M Camalli, J. Appl. Cryst. 1994, 27, 435.

[16]  P. W. Betteridge, J. R. Carruthers, R. I. Cooper, K. Prout, D. J. Watkin, J. Appl. Cryst. 2003, 36, 1487.
         | Crossref | GoogleScholarGoogle Scholar |