title: Dynamic kinetic resolution of atropisomeric amides.
abstract: [reaction: see text] Using L-proline as catalyst in the asymmetric aldol reaction and a series of benzamides and naphthamides, we have accomplished a dynamic kinetic resolution that simultaneously establishes the stereochemistry of the atropisomeric amide's chiral axis and a stereogenic center. The enantioselectivities ranged from 82% to 95% and the diastereoselectivities from 2.1:1 to 7.0:1.
authors.affiliation: P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, USA.
authors.forename: Vincent
authors.initials: V
authors.lastname: Chan
authors.forename: Jeung Gon
authors.initials: JG
authors.lastname: Kim
authors.forename: Ciril
authors.initials: C
authors.lastname: Jimeno
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Walsh
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D006860:Hydrogen Bonding; D007700:Kinetics; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000577:Amides