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


  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.

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