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  • Title: Regiochemical control in the metal-catalyzed transposition of allylic silyl ethers.
    Author: Hansen EC, Lee D.
    Journal: J Am Chem Soc; 2006 Jun 28; 128(25):8142-3. PubMed ID: 16787071.
    Abstract:
    A novel mode of regiochemical control over the allylic [1,3]-transposition of silyloxy groups catalyzed by Re2O7 has been developed. This strategy relies on a cis-oriented vinyl boronate, generated from the Alder-ene reaction of homoallylic silyl ethers and alkynyl boronates, to trap out the allylic hydroxyl group. The resulting cyclic boronic acids are excellent partners for cross-coupling reactions. High chirality transfer is observed for the rearrangement of enantioenriched allylic silyl ethers.
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