title: Enantioselective zinc/BINOL-catalysed alkynylation of aldimines generated in situ from α-amido sulfones.
abstract: Chiral nonracemic N-Cbz-protected propargylic amines have been prepared by the addition of terminal alkynes to imines generated in situ from α-amido sulfones in the presence of diethylzinc and BINOL-type ligands as catalysts. The reactions give good yields and high enantioselectivities (ee values up to 95 %) for a good number of aromatic and heteroaromatic α-amido sulfones and alkynes.
authors.affiliation: Departament de Química Orgànica, Facultat de Química, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot, Spain.
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Blay
authors.forename: Ana
authors.initials: A
authors.lastname: Brines
authors.forename: Alicia
authors.initials: A
authors.lastname: Monleón
authors.forename: José R
authors.initials: JR
authors.lastname: Pedro
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D009284:Naphthols / Q000737:chemistry*; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones; D015032:Zinc / Q000737:chemistry*
chemical_list: D000480:Alkynes; D000588:Amines; C406944:BINOL, naphthol; D008024:Ligands; D009284:Naphthols; D009942:Organometallic Compounds; D013450:Sulfones; D015032:Zinc