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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

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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.