Andrew, R. J., Mellor, J. M. and Reid, G.
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), . (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.
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