title: Photoredox α-vinylation of α-amino acids and N-aryl amines.
abstract: A new coupling protocol has been developed that allows the union of vinyl sulfones with photoredox-generated α-amino radicals to provide allylic amines of broad diversity. Direct C-H vinylations of N-aryl tertiary amines, as well as decarboxylative vinylations of N-Boc α-amino acids, proceed in high yield and with excellent olefin geometry control. The utility of this new allyl amine forming reaction has been demonstrated via the syntheses of several natural products and a number of established pharmacophores.
authors.affiliation: Merck Center for Catalysis at Princeton University , Princeton, New Jersey 08544, United States.
authors.forename: Adam
authors.initials: A
authors.lastname: Noble
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D055668:Photochemical Processes
chemical_list: D000475:Alkenes; D000588:Amines; D000596:Amino Acids