title: Enantiospecific sp(2)-sp(3) coupling of secondary and tertiary boronic esters.
abstract: The cross-coupling of boronic acids and related derivatives with sp(2) electrophiles (the Suzuki-Miyaura reaction) is one of the most powerful C-C bond formation reactions in synthesis, with applications that span pharmaceuticals, agrochemicals and high-tech materials. Despite the breadth of its utility, the scope of this Nobel prize-winning reaction is rather limited when applied to aliphatic boronic esters. Primary organoboron reagents work well, but secondary and tertiary boronic esters do not (apart from a few specific and isolated examples). Through an alternative strategy, which does not involve using transition metals, we have discovered that enantioenriched secondary and tertiary boronic esters can be coupled to electron-rich aromatics with essentially complete enantiospecificity. As the enantioenriched boronic esters are easily accessible, this reaction should find considerable application, particularly in the pharmaceutical industry where there is growing awareness of the importance of, and greater clinical success in, creating biomolecules with three-dimensional architectures.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Amadeu
authors.initials: A
authors.lastname: Bonet
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Marcin
authors.initials: M
authors.lastname: Odachowski
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Daniele
authors.initials: D
authors.lastname: Leonori
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Stephanie
authors.initials: S
authors.lastname: Essafi
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.
authors.forename: Varinder K
authors.initials: VK
authors.lastname: Aggarwal
mesh_terms: D001895:Boron / Q000737:chemistry*; D001897:Boronic Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001897:Boronic Acids; D004952:Esters; D001895:Boron