title: Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes.
abstract: The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (-)-bursehernin.
authors.affiliation: Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544-1009 (USA) http://www.princeeton.edu/chemistry/macmillan/
authors.forename: Eric R
authors.initials: ER
authors.lastname: Welin
authors.affiliation: Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544-1009 (USA) http://www.princeeton.edu/chemistry/macmillan/
authors.forename: Alexander A
authors.initials: AA
authors.lastname: Warkentin
authors.affiliation: Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544-1009 (USA) http://www.princeeton.edu/chemistry/macmillan/
authors.forename: Jay C
authors.initials: JC
authors.lastname: Conrad
authors.affiliation: Merck Center for Catalysis at Princeton University, Washington Road, Princeton, NJ 08544-1009 (USA) http://www.princeeton.edu/chemistry/macmillan/. dmacmill@princeton.edu.
authors.forename: David W C
authors.initials: DW
authors.lastname: MacMillan
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000478:Alkylation; D001688:Biological Products / Q000138:chemical synthesis*; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis*; D017705:Lignans / Q000138:chemical synthesis*; D008958:Models, Molecular; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001688:Biological Products; D007783:Lactones; D017705:Lignans; C023816:bursehernin
keywords: aldehydes; alkylation; organocatalysis; photoredox catalysis; total synthesis