title: Asymmetric alkynylation of aldehydes with propiolates without high reagent loading and any additives.
abstract: The asymmetric alkynylation of aliphatic and aromatic aldehydes with propiolates was mediated by dialkylzinc and a novel prolinol catalyst without high reagent loading and any additives, such as Ti(Oi-Pr)(4), to give the corresponding γ-hydroxy-α,β-acetylenic esters with high enantiomeric excess of up to 95%.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0879, Japan. kojima@phs.osaka-u.ac.jp
authors.forename: Naoto
authors.initials: N
authors.lastname: Kojima
authors.forename: Shogo
authors.initials: S
authors.lastname: Nishijima
authors.forename: Kaoru
authors.initials: K
authors.lastname: Tsuge
authors.forename: Tetsuaki
authors.initials: T
authors.lastname: Tanaka
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis / Q000187:drug effects; D002625:Chemistry, Organic; D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011422:Propionates / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D012996:Solutions; D013237:Stereoisomerism; D017967:Zinc Compounds / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000480:Alkynes; D004952:Esters; D009942:Organometallic Compounds; D011422:Propionates; D011759:Pyrrolidines; D012996:Solutions; D017967:Zinc Compounds; C010509:prolinol; C011537:propiolic acid