Highly functionalised difluorinated cyclohexenols

Crowley, P J and Moralee, A.C. and Percy, Jonathan and Spencer, N.S. (2000) Highly functionalised difluorinated cyclohexenols. Synlett, 2000 (12). pp. 1737-1740. ISSN 0936-5214 (https://doi.org/10.1055/s-2000-8688)

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.

ORCID iDs

Percy, Jonathan ORCID: https://orcid.org/0000-0001-8636-2704

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• Item metadata

  Item type:	Article
  ID code:	38927
  Dates:	Date Event 2000 Published
  Subjects:	Science > Chemistry
  Department:	Faculty of Science > Pure and Applied Chemistry
  Depositing user:	Pure Administrator
  Date deposited:	04 Apr 2012 08:25
  Last modified:	11 Nov 2024 10:06
  URI:	https://strathprints.strath.ac.uk/id/eprint/38927