Audouard, Christophe and Fawcett, John and Griffith, Gerry A and Kerouredan, Erwan and Miah, Afjal Hussain and Percy, Jonathan and Yang, Hongli (2004) A potentially divergent and rapid route to analogues of deoxycyclitols, pentopyranoses, 6-deoxyhexoses, and hexoses. Organic Letters, 6 (23). pp. 4269-4272. ISSN 1523-7060Full text not available in this repository. (Request a copy from the Strathclyde author)
Direct precursors to analogues of pentopyranoses, 6-deoxyhexoses, and hexoses, in which a CF2 center replaces the pyranose oxygen, have been synthesized rapidly from trifluoroethanol. A simple scaleable allylation reaction delivers ethers which undergo dehydrofluorination/metalation, followed by addition to either acrolein or cinnamaldehyde, to afford allylic alcohols. Fluorine-assisted [3,3]-rearrangement followed by reduction with sodium borohydride delivers diols, which undergo RCM smoothly to afford cyclohexene diols.
|Keywords:||pentopyranoses, 6-deoxyhexoses, hexoses, Chemistry, Biochemistry, Organic Chemistry, Physical and Theoretical Chemistry|
|Subjects:||Science > Chemistry|
|Department:||Faculty of Science > Pure and Applied Chemistry|
|Depositing user:||Pure Administrator|
|Date Deposited:||04 Apr 2012 14:46|
|Last modified:||05 May 2016 00:22|