title: Enantioselective direct α-amination of aldehydes via a photoredox mechanism: a strategy for asymmetric amine fragment coupling.
abstract: The direct, asymmetric α-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis. Photon-generated N-centered radicals undergo enantioselective α-addition to catalytically formed chiral enamines to directly produce stable α-amino aldehyde adducts bearing synthetically useful amine substitution patterns. Incorporation of a photolabile group on the amine precursor obviates the need to employ a photoredox catalyst in this transformation. Importantly, this photoinduced transformation allows direct and enantioselective access to α-amino aldehyde products that do not require postreaction manipulation.
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Cecere
authors.forename: Christian M
authors.initials: CM
authors.lastname: König
authors.forename: Jennifer L
authors.initials: JL
authors.lastname: Alleva
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D010084:Oxidation-Reduction; D017785:Photons; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000588:Amines