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Issue 5, 2016
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Sustainable synthesis of enantiopure fluorolactam derivatives by a selective direct fluorination – amidase strategy

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Abstract

Pharmaceutically important chiral fluorolactam derivatives bearing a fluorine atom at a stereogenic centre were synthesized by a route involving copper catalyzed selective direct fluorination using fluorine gas for the construction of the key C–F bond and a biochemical amidase process for the crucial asymmetric cyclisation stage. A comparison of process green metrics with reported palladium catalyzed enantioselective fluorination methodology shows the fluorination-amidase route to be very efficient and more suitable for scale-up.

Graphical abstract: Sustainable synthesis of enantiopure fluorolactam derivatives by a selective direct fluorination – amidase strategy

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Publication details

The article was received on 15 Sep 2015, accepted on 13 Oct 2015 and first published on 13 Oct 2015


Article type: Paper
DOI: 10.1039/C5GC02209F
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Citation: Green Chem., 2016,18, 1313-1318
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    Sustainable synthesis of enantiopure fluorolactam derivatives by a selective direct fluorination – amidase strategy

    N. J. Willis, C. A. Fisher, C. M. Alder, A. Harsanyi, L. Shukla, J. P. Adams and G. Sandford, Green Chem., 2016, 18, 1313
    DOI: 10.1039/C5GC02209F

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