title: Direct enantioselective three-component synthesis of optically active propargylamines in water.
abstract: An enantioselective three-component reaction of aldehydes, amines, and alkynes in water by using a bis(imidazoline)-Cu(I) catalysts having a hydrophobic substituent and sodium dodecyl sulfate as a surfactant was developed. The reaction was applied to a broad range of aldehydes and alkynes to give optically active propargylamines with excellent yields (up to 99 %) and enantiomeric excesses (up to 99 % ee).
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245.
authors.forename: Mutsuyo
authors.initials: M
authors.lastname: Ohara
authors.forename: Yoshichika
authors.initials: Y
authors.lastname: Hara
authors.forename: Tohru
authors.initials: T
authors.lastname: Ohnuki
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakamura
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011437:Propylamines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000480:Alkynes; D000588:Amines; D011437:Propylamines; D014867:Water; C009054:propargylamine; D003300:Copper; D010293:Pargyline
keywords: alkynylation; enantioselectivity; propargylamines; three-component reaction; water