title: Organocatalytic enantioselective decarboxylative reaction of malonic acid half thioesters with cyclic N-sulfonyl ketimines by using N-heteroarenesulfonyl cinchona alkaloid amides.
abstract: The organocatalytic enantioselective decarboxylative Mannich reaction of malonic acid half thioesters (MAHTs) with cyclic N-sulfonyl ketimines by using N-heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. The reaction proceeds through a nucleophilic addition of the MAHTs to the ketimines prior to decarboxylation.
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555 (Japan). snakamur@nitech.ac.jp.
authors.forename: Shuichi
authors.initials: S
authors.lastname: Nakamura
authors.forename: Masahide
authors.initials: M
authors.lastname: Sano
authors.forename: Ayaka
authors.initials: A
authors.lastname: Toda
authors.forename: Daisuke
authors.initials: D
authors.lastname: Nakane
authors.forename: Hideki
authors.initials: H
authors.lastname: Masuda
mesh_terms: D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D003653:Decarboxylation; D007097:Imines / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: D000577:Amides; D002930:Cinchona Alkaloids; D007097:Imines; D008314:Malonates; D009570:Nitriles; D013457:Sulfur Compounds; C542835:ketimine; C030290:malonic acid
keywords: Mannich reaction; enantioselectivity; organocatalysis; quaternary stereocenters