First Regio- and Enantioselective Chromium-Catalyzed Homoallenylation of Aldehydes

Authors

  • Vincent Coeffard Dr.,

    1. Centre for Synthesis and Chemical Biology (CSCB), School of Chemistry and Chemical Biology, Conway Institute of Biomolecular Research, University College Dublin, Belfield, Dublin 4 (Ireland), Fax: (+353) 1-716-2501
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  • Miriam Aylward,

    1. Centre for Synthesis and Chemical Biology (CSCB), School of Chemistry and Chemical Biology, Conway Institute of Biomolecular Research, University College Dublin, Belfield, Dublin 4 (Ireland), Fax: (+353) 1-716-2501
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  • Patrick J. Guiry Prof.

    1. Centre for Synthesis and Chemical Biology (CSCB), School of Chemistry and Chemical Biology, Conway Institute of Biomolecular Research, University College Dublin, Belfield, Dublin 4 (Ireland), Fax: (+353) 1-716-2501
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  • We thank Science Foundation Ireland for the award of a postdoctoral scholarship (054/RFP4/CHE/0075) for V.C. and the Irish Research Council for Science Engineering and Technology (RS/2006/6) for a grant to M.A. We also acknowledge financial support from the Centre for Synthesis and Chemical Biology, which was funded by the Higher Education Authority’s Programme for Research in Third-Level Institutions (PRTLI).

Abstract

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Game, set, and match: The first regio- and enantioselective version of the title reaction is described. The chiral catalyst prepared in situ from CrCl3 and a non-C2-symmetric bis(oxazoline) ligand 1 affords the valuable chiral β-allenols regioselectively in good yields with excellent ee values. R=aryl, alkyl.

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