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 0936-5214Full text not available in this repository. (Request a copy from the Strathclyde author)
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.
|Keywords:||difluoroalkenoate, fluorinated dienophile, Stille, Diels-Alder , ring opening, Chemistry, Organic Chemistry|
|Subjects:||Science > Chemistry|
|Department:||Faculty of Science > Pure and Applied Chemistry|
|Depositing user:||Pure Administrator|
|Date Deposited:||04 Apr 2012 08:25|
|Last modified:||05 May 2016 00:22|