title: Asymmetric thio-Michael/nucleophilic addition domino reaction with chiral N-sulfinimines.
abstract: Optically active N-sulfinimines underwent stereoselective Michael/nucleophilic addition domino reaction triggered by magnesium thiolate to give alpha-phenylthiomethyl-beta-(N-sulfinylamino) esters in high diastereomeric excess. The adducts were readily converted into optically active alpha-methylene-beta-(N-sulfinylamino)esters so that this reaction provides a useful asymmetric aza-Baylis-Hillman-equivalent method.
authors.affiliation: Department of Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, Ube 755-8611, Japan. ak10@yamaguchi-u.ac.jp
authors.forename: Akio
authors.initials: A
authors.lastname: Kamimura
authors.forename: Hidenori
authors.initials: H
authors.lastname: Okawa
authors.forename: Yuki
authors.initials: Y
authors.lastname: Morisaki
authors.forename: Shingo
authors.initials: S
authors.lastname: Ishikawa
authors.forename: Hidemitsu
authors.initials: H
authors.lastname: Uno
mesh_terms: D002625:Chemistry, Organic / Q000379:methods*; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013441:Sulfinic Acids / Q000737:chemistry*; D013455:Sulfur; D047090:beta-Lactams / Q000737:chemistry
chemical_list: D007097:Imines; D013441:Sulfinic Acids; D047090:beta-Lactams; D013455:Sulfur