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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

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
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
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.
addition, enamines, organofluorine, phenols, x-ray diffraction trifluoromethyl ketones, efficient synthesis
0040-4020
7255-7260
Andrew, R. J.
004eed6c-6a89-451a-9cd1-8e27ce59c9e4
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
Reid, G.
ff85ed93-1d4e-4c2b-a9b7-d927a61c4abe
Andrew, R. J.
004eed6c-6a89-451a-9cd1-8e27ce59c9e4
Mellor, J. M.
d9b993ad-31be-4f91-8ea3-1723cd1c23bc
Reid, G.
ff85ed93-1d4e-4c2b-a9b7-d927a61c4abe

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.

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: https://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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