title: Gadolinium-Catalyzed Regio- and Enantioselective Aminolysis of Aromatic trans-2,3-Epoxy Sulfonamides.
abstract: The first enantioselective aminolysis of aromatic trans-2,3-epoxy sulfonamides has been accomplished, which was efficiently catalyzed by a Gd-N,N'-dioxide complex. Under the directing effect of the sulfonamide moiety the ring-opening reaction proceeded selectively at the C-3 position in a highly enantioselective manner furnishing various Ts- and SES-protected 3-amino-3-phenylpropan-2-olamines as products.
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637 (USA).
authors.forename: Chuan
authors.initials: C
authors.lastname: Wang
authors.affiliation: Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637 (USA). yamamoto@uchicago.edu, hyamamoto@jsc.chubu.ac.jp.|Molecular Catalyst Research Center, Chubu University, 1200 Matsumoto, Kasugai, Aichi 487-8501 (Japan). yamamoto@uchicago.edu, hyamamoto@jsc.chubu.ac.jp.
authors.forename: Hisashi
authors.initials: H
authors.lastname: Yamamoto
mesh_terms: D000586:Amination; D000588:Amines / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D005682:Gadolinium / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000588:Amines; D000605:Amino Alcohols; D004852:Epoxy Compounds; D006841:Hydrocarbons, Aromatic; D013449:Sulfonamides; D005682:Gadolinium
keywords: amino alcohols; gadolinium-catalysis; kinetic resolution; regioselective; ring opening