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Issue 39, 2012
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Consecutive iridium catalyzed C–C and C–H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C–H (2-fluoro)allylation of primary alcohols

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Abstract

Commercially available (2-fluoro)allyl chloride serves as an efficient allyl donor in highly enantioselective iridium catalyzed carbonyl (2-fluoro)allylations from the alcohol or aldehyde oxidation level via transfer hydrogenation. Diastereoselective Crabtree hydrogenation of the resulting homoallylic alcohols provides syn-3-fluoro-1-alcohols.

Graphical abstract: Consecutive iridium catalyzed C–C and C–H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C–H (2-fluoro)allylation of primary alcohols

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Publication details

The article was received on 08 Mar 2012, accepted on 09 Mar 2012, published on 04 Apr 2012 and first published online on 04 Apr 2012


Article type: Communication
DOI: 10.1039/C2CC31743E
Citation: Chem. Commun., 2012,48, 4692-4694
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    Consecutive iridium catalyzed C–C and C–H bond forming hydrogenations for the diastereo- and enantioselective synthesis of syn-3-fluoro-1-alcohols: C–H (2-fluoro)allylation of primary alcohols

    A. Hassan, T. P. Montgomery and M. J. Krische, Chem. Commun., 2012, 48, 4692
    DOI: 10.1039/C2CC31743E

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