title: Intramolecular carbolithiation of heterosubstituted alkynes: an experimental and theoretical study.
abstract: A series of heterosubstitued alkynes was successfully submitted to the intramolecular carbolithiation of their triple bond. We show that the addition is stereoselective because of the control exerted by the terminal substituent X on the geometry of the transition state. A complementary DFT study suggests that the addition is anti when a strong Li-X interaction occurs.
authors.affiliation: Laboratoire COBRA, CNRS UMR 6014 & FR 3038, Univ. Rouen, INSA Rouen, 76821 Mt St Aignan Cedex (France).
authors.forename: Rudy
authors.initials: R
authors.lastname: Lhermet
authors.affiliation: Laboratoire COBRA, CNRS UMR 6014 & FR 3038, Univ. Rouen, INSA Rouen, 76821 Mt St Aignan Cedex (France).
authors.forename: Maha
authors.initials: M
authors.lastname: Ahmad
authors.affiliation: Laboratoire COBRA, CNRS UMR 6014 & FR 3038, Univ. Rouen, INSA Rouen, 76821 Mt St Aignan Cedex (France).
authors.forename: Clémence
authors.initials: C
authors.lastname: Hauduc
authors.affiliation: Laboratoire COBRA, CNRS UMR 6014 & FR 3038, Univ. Rouen, INSA Rouen, 76821 Mt St Aignan Cedex (France).
authors.forename: Catherine
authors.initials: C
authors.lastname: Fressigné
authors.affiliation: Laboratoire COBRA, CNRS UMR 6014 & FR 3038, Univ. Rouen, INSA Rouen, 76821 Mt St Aignan Cedex (France). muriel.durandetti@univ-rouen.fr.
authors.forename: Muriel
authors.initials: M
authors.lastname: Durandetti
authors.affiliation: Laboratoire COBRA, CNRS UMR 6014 & FR 3038, Univ. Rouen, INSA Rouen, 76821 Mt St Aignan Cedex (France). jmaddalu@crihan.fr.
authors.forename: Jacques
authors.initials: J
authors.lastname: Maddaluno
keywords: alkynes; carbenoids; cyclization; density functional calculations; lithiation