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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), pp. 7255-7260.

Record type: Article

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.

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More information

Published date: 8 September 2000
Keywords: addition, enamines, organofluorine, phenols, x-ray diffraction trifluoromethyl ketones, efficient synthesis

Identifiers

Local EPrints ID: 18905
URI: http://eprints.soton.ac.uk/id/eprint/18905
ISSN: 0040-4020
PURE UUID: 2482d911-17ff-445e-9d07-58eaf7503dea

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Date deposited: 16 Dec 2005
Last modified: 22 Oct 2017 03:22

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Contributors

Author: R. J. Andrew
Author: J. M. Mellor
Author: G. Reid

University divisions

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