title: Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.
abstract: Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C-N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS) under aerobic conditions has been developed. In combination with the enantioselective preparation of α-bromo nitroalkane donors, this protocol realizes the goal of enantioselective α-amino amide and peptide synthesis based solely on catalytic methods.
authors.affiliation: Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University , Nashville, Tennessee 37235, United States.
authors.forename: Kenneth E
authors.initials: KE
authors.lastname: Schwieter
authors.forename: Bo
authors.initials: B
authors.lastname: Shen
authors.forename: Jessica P
authors.initials: JP
authors.lastname: Shackleford
authors.forename: Matthew W
authors.initials: MW
authors.lastname: Leighty
authors.forename: Jeffrey N
authors.initials: JN
authors.lastname: Johnston
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D013388:Succinimides / Q000737:chemistry*
chemical_list: D000473:Alkanes; D000577:Amides; D000588:Amines; D006842:Hydrocarbons, Brominated; D009574:Nitro Compounds; D013388:Succinimides; C008155:N-iodosuccinimide; D010100:Oxygen