Stereoselective synthesis of substituted bicyclo- 3.3.1 -nonan-9-ones by additions of enamines of cyclohexanones to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one
Andrew, R. J., Mellor, J. M. and Reid, G. (2000) Stereoselective synthesis of substituted bicyclo- 3.3.1 -nonan-9-ones by additions of enamines of cyclohexanones to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one. Tetrahedron, 56, (37), 7255-7260. (doi:10.1016/S0040-4020(00)00596-2).
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Description/Abstract
Addition of the pyrrolidine enamine of cyclohexanone to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one affords a single diastereoisomer of 4-ethoxy-2-hydroxy-2-trifluoromethylbicyclo [3.3.1]nonan-9-one. Similarly the pyrrolidine enamine of 4-methylcyclohexanone also in a highly diastereoselective manner affords a single bicyclic ketone. In the latter case a single crystal X-ray diffraction analysis permits unambiguous determination of all stereochemical detail. Other examples of addition to 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one are discussed. The mechanistic explanation of the unusually high selectivity is discussed.
| Item Type: | Article |
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| Related URLs: | |
| Keywords: | addition, enamines, organofluorine, phenols, x-ray diffraction trifluoromethyl ketones, efficient synthesis |
| Subjects: | Q Science Q Science > QD Chemistry |
| Divisions: | University Structure - Pre August 2011 > School of Chemistry |
| Item ID: | 18905 |
| Date Deposited: | 16 Dec 2005 |
| Last Modified: | 01 Jun 2011 08:31 |
| Contributors: | Andrew, R. J. (Author) Mellor, J. M. (Author) Reid, G. (Author) |
| Date: | 8 September 2000 |
| Status: | Published |
| URI: | http://eprints.soton.ac.uk/id/eprint/18905 |
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