Timothy Ramadhar - Stereocontrolled Synthesis of Contiguous C(sp3)−C(aryl) Bonds by Lanthanide(III)-Catalyzed Domino Aryl-Claisen [3,3]-Sigmatropic Rearrangements

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      Publication Details (including relevant citation   information):

      Timothy R. Ramadhar, Jun-ichi Kawakami, Alan J. Lough, Robert A.   Batey. Organic Letters, 2010,   12, 4446-4449.


      A domino [3,3]-sigmatropic aryl-Claisen rearrangement of cyclic   and acyclic bisaryloxy-substituted alkenes can be performed in   high yield by using Ln(fod)3 catalysis to obtain   bisphenolic products incorporating two contiguous   aryl−C(sp3) bonds. Stereospecific rearrangement was   observed for cyclic substrates. The precursor diaryl ethers were   typically synthesized from the corresponding diols by double   arylation procedures using either copper catalyzed coupling of   aryltrifluoroborate salts or by SNAr reaction.

      Address (URL): http://dx.doi.org/10.1021/ol1018147