title: Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.
abstract: The first enantioselective aldehyde α-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantioselectivity. The utility of this methodology has been demonstrated via rapid access to an enantioenriched drug target for angiogenesis suppression.
authors.affiliation: Merck Center for Catalysis at Princeton University, Princeton, New Jersey 08544, USA.
authors.forename: Hui-Wen
authors.initials: HW
authors.lastname: Shih
authors.forename: Mark N
authors.initials: MN
authors.lastname: Vander Wal
authors.forename: Rebecca L
authors.initials: RL
authors.lastname: Grange
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D048289:Imidazolidines / Q000737:chemistry*; D007495:Iridium / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010777:Photochemistry; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D048289:Imidazolidines; D007495:Iridium