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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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Article information


Submitted
30 Sep 2003
Accepted
05 Nov 2003
First published
20 Nov 2003

Org. Biomol. Chem., 2004,2, 168-174
Article type
Paper

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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