Alexander Pulis - Enantioselective Synthesis and Cross-Coupling of Tertiary Propargylic Boronic Esters Using Lithiation-Borylation of Propargylic Carbamates

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      Publication Details (including relevant citation   information):

      Angew.   Chem. Int. Ed. 2012,   51, 11795-11799

        B. M. Partridge, L. Chausset-Boissarie, M. Burns,    A. P.   Pulis, and   V. K. Aggarwal

      DOI:     10.1002/anie.201203198

        Highlighted in SYNFACTS 2013, 9,   198

      Abstract:

      Lithiation–borylation   of propargylic carbamates leads to tertiary propargylic boronic   esters in very high e.r., provided that ethylene glycol boronic   esters are used. These versatile intermediates undergo a range of   highly stereoselective transformations, including   protodeboronation to give tertiary allenes and Suzuki–Miyaura   cross-couplings of tertiary boron species leading to   tetrasubstituted allenes with high enantiospecificity.

      Address (URL): http://onlinelibrary.wiley.com/doi/10.1002/anie.201203198/abstract