title: Preparation and Reactivity of Acyclic Chiral Allylzinc Species by a Zinc-Brook Rearrangement.
abstract: The zinc-Brook rearrangement of enantiomerically enriched α-hydroxy allylsilane produces a chiral allylzinc intermediate, which reacts with retention of configuration in the presence of an electrophile. Two remarkable features of this transformation are the stereochemical outcome during the formation of the allylzinc species and the complete stereocontrol in the organized six-membered transition state, which leads to an overall and complete transfer of chirality within the reaction sequence.
authors.affiliation: The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa, 32000, Israel.
authors.forename: Markus
authors.initials: M
authors.lastname: Leibeling
authors.affiliation: The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa, 32000, Israel.
authors.forename: Khriesto A
authors.initials: KA
authors.lastname: Shurrush
authors.affiliation: The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa, 32000, Israel.
authors.forename: Veronika
authors.initials: V
authors.lastname: Werner
authors.affiliation: ICBMS UMR 5246, Université de Lyon, Bât. Curien, 43 Bd du 11 Novembre 1918, 69622, Villeurbanne Cedex 5, France.
authors.forename: Lionel
authors.initials: L
authors.lastname: Perrin
authors.affiliation: The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry and Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa, 32000, Israel. chilanm@tx.technion.ac.il.
authors.forename: Ilan
authors.identifier: 0000-0001-9154-2320
authors.initials: I
authors.lastname: Marek
keywords: Brook rearrangement; allylic compounds; chirality; olefins; zinc