title: Enantioselective synthesis of α-oxy amides via Umpolung amide synthesis.
abstract: α-Oxy amides are prepared through enantioselective synthesis using a sequence beginning with a Henry addition of bromonitromethane to aldehydes and finishing with Umpolung Amide Synthesis (UmAS). Key to high enantioselection is the finding that ortho-iodo benzoic acid salts of the chiral copper(II) bis(oxazoline) catalyst deliver both diastereomers of the Henry adduct with high enantiomeric excess, homochiral at the oxygen-bearing carbon. Overall, this approach to α-oxy amides provides an innovative complement to alternatives that focus almost entirely on the enantioselective synthesis of α-oxy carboxylic acids.
authors.affiliation: Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, USA.
authors.forename: Matthew W
authors.initials: MW
authors.lastname: Leighty
authors.forename: Bo
authors.initials: B
authors.lastname: Shen
authors.forename: Jeffrey N
authors.initials: JN
authors.lastname: Johnston
mesh_terms: D000577:Amides / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000577:Amides