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 1523-7060
Full text not available in this repository. (Request a copy from the Strathclyde author)Abstract
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.
| Item type: | Article |
|---|---|
| ID code: | 38961 |
| Keywords: | pentopyranoses, 6-deoxyhexoses, hexoses, Chemistry |
| Subjects: | Science > Chemistry |
| Department: | Faculty of Science > Pure and Applied Chemistry |
| Related URLs: | |
| Depositing user: | Pure Administrator |
| Date Deposited: | 04 Apr 2012 15:46 |
| Last modified: | 04 Apr 2012 15:46 |
| URI: | http://strathprints.strath.ac.uk/id/eprint/38961 |
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