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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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.
|Keywords:||addition, enamines, organofluorine, phenols, x-ray diffraction trifluoromethyl ketones, efficient synthesis|
Q Science > QD Chemistry
|Divisions:||University Structure - Pre August 2011 > School of Chemistry
|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|
|RDF:||RDF+N-Triples, RDF+N3, RDF+XML, Browse.|
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