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Highly Enantioselective Synthesis of Tertiary Boronic Esters and their Stereospecific Conversion to other Functional Groups and Quaternary Stereocentres

Authors

  • Helen K. Scott,

    1. School of Chemistry, University of Bristol, Cantocks Close, Bristol, BS8 1TS (UK), Fax: (+44) 117-925-1295
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  • Prof.  Varinder K. Aggarwal

    Corresponding author
    1. School of Chemistry, University of Bristol, Cantocks Close, Bristol, BS8 1TS (UK), Fax: (+44) 117-925-1295
    • School of Chemistry, University of Bristol, Cantocks Close, Bristol, BS8 1TS (UK), Fax: (+44) 117-925-1295
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Abstract

Organoboron compounds are useful in asymmetric synthesis. We have developed an efficient methodology for the highly enantioselective synthesis of tertiary boronic esters from the corresponding secondary benzylic alcohols. Further stereospecific transformations of the boronic ester moiety are described including the preparation of tertiary alcohols, C-tertiary amines and tertiary arylalkanes. Several homologations of tertiary boronic esters have also been developed for the construction of quaternary stereocentres.

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