Application of Vinyl Nucleophiles in Matteson Homologations
Thorsten Kinsinger, Uli Kazmaier
Abstract
The Matteson homologation with vinyl nucleophiles was found to be a versatile tool for the synthesis of highly substituted and functionalized allyl boronic esters. High yields and stereoselectivities are obtained with sterically demanding alkyl boronic esters and/or Grignard reagents. With the application of such vinyl Matteson homologations, the polyketide fragment of lagunamide B is synthesized.
Topics & Concepts
ChemistryNucleophileSteric effectsReagentAlkylOrganic chemistryCombinatorial chemistryCatalysisSynthetic Organic Chemistry MethodsAdvanced Synthetic Organic ChemistryAsymmetric Synthesis and Catalysis