title: Direct asymmetric Mannich-type reaction of α-isocyanoacetates with ketimines using cinchona alkaloid/copper(II) catalysts.
abstract: The enantioselective direct Mannich-type reaction of ketimines with α-isocyanoacetates has been developed. Excellent yields and enantioselectivity were observed for the reaction of various ketimines and α-isocyanoacetates using cinchona alkaloid/Cu(OTf)2 and a base. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. This process offers an efficient route for the synthesis of α,β-diamino acids.
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan) http://www.ach.nitech.ac.jp/∼organic/nakamura/index.html.
authors.forename: Masashi
authors.initials: M
authors.lastname: Hayashi
authors.forename: Masaru
authors.initials: M
authors.lastname: Iwanaga
authors.forename: Noriyuki
authors.initials: N
authors.lastname: Shiomi
authors.forename: Daisuke
authors.initials: D
authors.lastname: Nakane
authors.forename: Hideki
authors.initials: H
authors.lastname: Masuda
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakamura
mesh_terms: D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000085:Acetates; D002930:Cinchona Alkaloids; D007097:Imines; D009570:Nitriles; C542835:ketimine
keywords: Lewis acid; alkaloids; asymmetric synthesis; copper; organocatalysis