Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes: synthesis of a fragment of (+)-vibsanin A

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Abstract Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.

Journal

  • Tetrahedron

    Tetrahedron 72 (35), 5465-5471, 2016-09

    Elsevier BV

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