title: Selective vinyl C-H lithiation of cis-stilbenes.
abstract: A stereochemistry-controlled suppression of carbolithiation facilitated a regioselective vinyl C-H lithiation of cis-stilbenes allowing routine regio- and stereoselective access to polysubstituted alkenes and heterocycles. This unique selectivity was obtained for numerous directing groups and could be rationalized with DFT computational studies and an experimental mechanistic illustration of a unique anion migration.
authors.affiliation: Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland.
authors.forename: Thomas
authors.initials: T
authors.lastname: Tricotet
authors.forename: Patricia
authors.initials: P
authors.lastname: Fleming
authors.forename: Juliet
authors.initials: J
authors.lastname: Cotter
authors.forename: Anne-Marie L
authors.initials: AM
authors.lastname: Hogan
authors.forename: Carsten
authors.initials: C
authors.lastname: Strohmann
authors.forename: Viktoria H
authors.initials: VH
authors.lastname: Gessner
authors.forename: Donal F
authors.initials: DF
authors.lastname: O'Shea
mesh_terms: D018360:Crystallography, X-Ray; D008094:Lithium / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013267:Stilbenes / Q000737:chemistry*
chemical_list: D009942:Organometallic Compounds; D013267:Stilbenes; D008094:Lithium