title: Direct Enantioselective Vinylogous Mannich Reaction of Ketimines with γ-Butenolide by Using Cinchona Alkaloid Amide/Zinc(II) Catalysts.
abstract: A direct enantioselective vinylogous Mannich reaction of ketimines with γ-butenolide has been developed. Good yields and enantioselectivities were observed for the reaction of various ketimines by using a cinchona alkaloid amide/Zn(OTf)2 catalyst and Et3N. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts.
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245http://www.ach.nitech.ac.jp/∼organic/nakamura/index.html. snakamur@nitech.ac.jp.
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakamura
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245http://www.ach.nitech.ac.jp/∼organic/nakamura/index.html.
authors.forename: Ryota
authors.initials: R
authors.lastname: Yamaji
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan), Fax: (+81) 52-735-5245http://www.ach.nitech.ac.jp/∼organic/nakamura/index.html.
authors.forename: Masashi
authors.initials: M
authors.lastname: Hayashi
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000577:Amides; D002930:Cinchona Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D002930:Cinchona Alkaloids; D007097:Imines; D008698:Mesylates; D009570:Nitriles; C542835:ketimine; C004511:butenolide; C012077:trifluoromethanesulfonic acid; D015107:4-Butyrolactone
keywords: Lewis acids; asymmetric synthesis; cinchona alkaloids; ketimines; γ-butenolides