Highly functionalised difluorinated cyclohexenols

P J Crowley, A.C. Moralee, Jonathan Percy, N.S. Spencer

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Alkenoate 5 prepared on a multigramme scale from trifluoroethanol underwent cycloaddition with furan in good yield. Reduction of the ester group in the endo-cycloadduct 7a with DIBAl-H also resulted in decarbamoylation to reveal a diol which was protected as an acetonide 10. Various methods for nucleophilic ring opening were explored releasing highly functionalised difluorinated cyclohexenols, and suggesting a novel route to difluorinated analogues of cyclitols and monosaccharides.
LanguageEnglish
Pages1737-1740
Number of pages4
JournalSynlett
Volume2000
Issue number12
DOIs
Publication statusPublished - 2000

Fingerprint

Cyclitols
Trifluoroethanol
Cycloaddition
Monosaccharides
Esters
furan

Keywords

  • difluoroalkenoate
  • fluorinated dienophile
  • Stille
  • Diels-Alder
  • ring opening

Cite this

Crowley, P. J., Moralee, A. C., Percy, J., & Spencer, N. S. (2000). Highly functionalised difluorinated cyclohexenols. Synlett, 2000(12), 1737-1740 . https://doi.org/10.1055/s-2000-8688
Crowley, P J ; Moralee, A.C. ; Percy, Jonathan ; Spencer, N.S. / Highly functionalised difluorinated cyclohexenols. In: Synlett. 2000 ; Vol. 2000, No. 12. pp. 1737-1740 .
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Crowley, PJ, Moralee, AC, Percy, J & Spencer, NS 2000, 'Highly functionalised difluorinated cyclohexenols' Synlett, vol. 2000, no. 12, pp. 1737-1740 . https://doi.org/10.1055/s-2000-8688

Highly functionalised difluorinated cyclohexenols. / Crowley, P J; Moralee, A.C.; Percy, Jonathan; Spencer, N.S.

In: Synlett, Vol. 2000, No. 12, 2000, p. 1737-1740 .

Research output: Contribution to journalArticle

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AU - Moralee, A.C.

AU - Percy, Jonathan

AU - Spencer, N.S.

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KW - difluoroalkenoate

KW - fluorinated dienophile

KW - Stille

KW - Diels-Alder

KW - ring opening

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DO - 10.1055/s-2000-8688

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Crowley PJ, Moralee AC, Percy J, Spencer NS. Highly functionalised difluorinated cyclohexenols. Synlett. 2000;2000(12):1737-1740 . https://doi.org/10.1055/s-2000-8688