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Issue 2, 2004
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Reactive resin facilitated preparation of an enantiopure fluorobicycloketone

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Abstract

A facile preparation of enantiopure ethyl (1S,5S,6S)-6-fluoro-2-oxobicyclo[3.1.0]hexane-6-carboxylate 1 is described. The key feature of the synthesis involves copper-catalyzed enantioselective intramolecular cyclopropanation of a diazoketone to form endo-fluorocyclopropane 1 in a single operation. Removal of a problematic chloroketone impurity using a reactive resin treatment enabled a high throughput enantiopurity upgrade by chiral HPLC. The development of a scalable synthesis of 1 is presented, including details of the selection of catalyst and ligand optimization, incorporation of a reactive resin treatment and selection of chiral HPLC media and conditions.

Graphical abstract: Reactive resin facilitated preparation of an enantiopure fluorobicycloketone

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Publication details

The article was received on 30 Sep 2003, accepted on 05 Nov 2003 and first published on 20 Nov 2003


Article type: Paper
DOI: 10.1039/B312180C
Citation: Org. Biomol. Chem., 2004,2, 168-174

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    Reactive resin facilitated preparation of an enantiopure fluorobicycloketone

    A. Wong, C. J. Welch, J. T. Kuethe, E. Vazquez, M. Shaimi, D. Henderson, I. W. Davies and D. L. Hughes, Org. Biomol. Chem., 2004, 2, 168
    DOI: 10.1039/B312180C

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