title: Stereospecific Coupling of Boronic Esters with N-Heteroaromatic Compounds.
abstract: A protocol for the stereospecific coupling of chiral secondary and tertiary boronic esters with lithiated N-heteroaromatics is described. The process involves initial boronate complex formation followed by addition of Troc-Cl, which activates the nitrogen and induces 1,2-migration. Oxidative workup furnishes the coupled product with >98% es.
authors: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, U.K.
authors: Josep
authors: J
authors: Llaveria
authors: School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, U.K.
authors: Daniele
authors: D
authors: Leonori
authors: School of Chemistry, University of Bristol , Cantock's Close, Bristol BS8 1TS, U.K.
authors: Varinder K
authors: VK
authors: Aggarwal
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001897:Boronic Acids; D004952:Esters; D006571:Heterocyclic Compounds; D006841:Hydrocarbons, Aromatic