title: Enantioselective intramolecular propargylic amination using chiral copper-pybox complexes as catalysts.
abstract: Intramolecular propargylic amination of propargylic acetates bearing an amino group at the suitable position in the presence of chiral copper-pybox complexes proceeds enantioselectively to give optically active 1-ethynyl-isoindolines (up to 98% ee). The method described in this communication provides a useful synthetic approach to the enantioselective preparation of nitrogen containing heterocyclic compounds with an ethynyl group at the α-position.
authors.affiliation: Institute of Engineering Innovation, School of Engineering, The University of Tokyo, Yayoi, Bunkyo-ku, Tokyo, 113-8656, Japan. ynishiba@sogo.t.u-tokyo.ac.jp.
authors.forename: Masashi
authors.initials: M
authors.lastname: Shibata
authors.forename: Kazunari
authors.initials: K
authors.lastname: Nakajima
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Nishibayashi
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D010080:Oxazoles / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C530038:(4'S,5'S)-2,6-bis(4'-(triisopropylsilyl)oxymethyl-5'-phenyl-1',3'-oxazolin-2'-yl)pyridine; D000480:Alkynes; D006571:Heterocyclic Compounds; D010080:Oxazoles; D020005:Propanols; D011725:Pyridines; D003300:Copper; C028255:propargyl alcohol