title: Ate complexes of secondary boronic esters as chiral organometallic-type nucleophiles for asymmetric synthesis.
abstract: The addition of an aryllithium reagent to a secondary boronic ester leads to an intermediate boron-ate complex that behaves as a chiral nucleophile, reacting with a broad range of electrophiles with inversion of stereochemistry. Depending on the electrophile, the C-B bond can be converted into C-I, C-Br, C-Cl, C-N, C-O, and C-C, all with very high levels of stereocontrol. This discovery now adds a new, readily available, configurationally stable, chiral organometallic-type reagent to the arsenal of methods for use in asymmetric organic synthesis.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Robin
authors.initials: R
authors.lastname: Larouche-Gauthier
authors.forename: Tim G
authors.initials: TG
authors.lastname: Elford
authors.forename: Varinder K
authors.initials: VK
authors.lastname: Aggarwal