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Enantioselective Synthesis of Branched Allylic Esters via Rhodium-Catalyzed Coupling of Allenes with Carboxylic Acids

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    Enantioselective Synthesis of Branched Allylic Esters via Rhodium-Catalyzed Coupling of Allenes with Carboxylic Acids
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    Institut für Organische Chemie und Biochemie, Freiburg Institute for Advanced Studies (FRIAS), Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79104 Freiburg im Breisgau, Germany
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    Cite this: J. Am. Chem. Soc. 2011, 133, 51, 20746–20749
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    https://doi.org/10.1021/ja210149g
    Published November 23, 2011
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    Abstract

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    We report on the first intermolecular asymmetric catalytic regio- and enantioselective addition of carboxylic acids to terminal allenes to form valuable branched allylic esters, employing a rhodium(I)/(R,R)-DIOP catalyst system.

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    Experimental procedures and analytic data for synthesized allenes and new compounds, including 1H NMR and 13C NMR spectra as well as scanned HPLC data sheets for chiral compounds. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2011, 133, 51, 20746–20749
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    https://doi.org/10.1021/ja210149g
    Published November 23, 2011
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