title: A general copper-BINAP-catalyzed asymmetric propargylation of ketones with propargyl boronates.
abstract: An operationally simple copper-BINAP-catalyzed, highly enantioselective propargylation of ketones is presented. The methodology was developed as an enantioselective process for methyl ethyl ketone and shown to be applicable to a wide variety of prochiral ketones. The resulting homopropargyl adducts are versatile latent carbonyls from which γ-butyrolactones, β-hydroxy methyl ketones, and β-hydroxycarboxylates are readily obtained.
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. keith.fandrick@boehringer-ingelheim.com
authors.forename: Keith R
authors.initials: KR
authors.lastname: Fandrick
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Fandrick
authors.forename: Jonathan T
authors.initials: JT
authors.lastname: Reeves
authors.forename: Joe
authors.initials: J
authors.lastname: Gao
authors.forename: Shengli
authors.initials: S
authors.lastname: Ma
authors.forename: Wenjie
authors.initials: W
authors.lastname: Li
authors.forename: Heewon
authors.initials: H
authors.lastname: Lee
authors.forename: Nelu
authors.initials: N
authors.lastname: Grinberg
authors.forename: Bruce
authors.initials: B
authors.lastname: Lu
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D001897:Boronic Acids / Q000737:chemistry*; D002074:Butanones / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D009281:Naphthalenes / Q000737:chemistry*; D010293:Pargyline / Q000737:chemistry
chemical_list: C406943:BINAP, 2-naphthol; D001897:Boronic Acids; D002074:Butanones; D007659:Ketones; D009281:Naphthalenes; C005222:methylethyl ketone; D003300:Copper; D010293:Pargyline