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  • Title: Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction.
    Author: Chemler SR, Danishefsky SJ.
    Journal: Org Lett; 2000 Aug 24; 2(17):2695-8. PubMed ID: 10990430.
    Abstract:
    [reaction: see text]Transannular macrocyclizations via intramolecular B-alkyl Suzuki reactions are described. Regioselective terminal olefin hydroboration with 9-BBN followed by Pd(0)-catalyzed Suzuki reaction in the presence of a base such as TlOEt at high dilution generates macrocycles with a high degree of control over olefin geometry with isomerically pure E or Z vinyl iodide substrates. These reactions are complementary to ring closing metathesis (RCM) macrocyclizations and may prove superior in cases where control of olefin geometry is required.
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