title: Enantio and diastereoselective addition of phenylacetylene to racemic α-chloroketones.
abstract: In this report, we have presented the first diastereoselective addition of phenylacetylene to chiral racemic chloroketones. The addition is controlled by the reactivity of the chloroketones that allowed the stereoselective reaction to be performed at -20 °C. Chiral racemic chloroketones are used in the reaction. By carefully controlling the temperature and the reaction time we were able to isolate the corresponding products in moderate yields and with good, simple and predictable facial stereoselection. Our reaction is a rare example of the use of chiral ketones in an enantioselective alkynylation reaction and opens new perspectives for the formation of chiral quaternary stereocenters.
authors.affiliation: Alma Mater Studiorum, Dipartimento di Chimica "G: Ciamician", Università di Bologna, Via Selmi 2, 40126 Bologna, Italy.
authors.forename: Silvia
authors.initials: S
authors.lastname: Alesi
authors.forename: Enrico
authors.initials: E
authors.lastname: Emer
authors.forename: Montse Guiteras
authors.initials: MG
authors.lastname: Capdevila
authors.forename: Diego
authors.initials: D
authors.lastname: Petruzziello
authors.forename: Andrea
authors.initials: A
authors.lastname: Gualandi
authors.forename: Pier Giorgio
authors.initials: PG
authors.lastname: Cozzi
mesh_terms: D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D008024:Ligands; D019906:Nuclear Magnetic Resonance, Biomolecular; D055601:Organic Chemistry Phenomena; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D008024:Ligands; C044736:phenylacetylene; D000114:Acetylene