title: Organocatalytic asymmetric synthesis of propargylamines with two adjacent stereocenters: mannich-type reactions of in situ generated C-alkynyl imines with β-keto esters.
abstract: Side by side: The title reaction is catalyzed by the chiral Brønsted acid (S)-1, and affords hitherto less accessible chiral propargylamines, having two adjacent stereocenters, in good to excellent diastereo- and enantioselectivities. Boc=tert-butoxycarbonyl.
authors.affiliation: Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo, Kyoto 606-8502 (Japan).
authors.forename: Taichi
authors.initials: T
authors.lastname: Kano
authors.forename: Taiga
authors.initials: T
authors.lastname: Yurino
authors.forename: Keiji
authors.initials: K
authors.lastname: Maruoka
mesh_terms: D002384:Catalysis; D004952:Esters; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011437:Propylamines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D007097:Imines; D011437:Propylamines; C009054:propargylamine; D010293:Pargyline
keywords: amines; asymmetric catalysis; imines; organocatalysis; synthetic methods