Organocatalytic asymmetric vinylogous addition to quinones - formation of optically active alpha-aryl ketones.
The first organocatalytic addition of dicyanoalkylidenes to quinones catalyzed by Cinchona alkaloids leading to formation of 1,4-diketone derivatives with high diastereomeric ratios (up to >98 : <2 dr) and enantioselectivities (up to 99% ee) has been developed; the optically active compounds obtained are useful for a number of transformations, e.g. the synthesis of optically active alpha-aryl ketones.
Alemán
José
J
Danish National Research Foundation: Center for Catalysis, Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark.
Jacobsen
Christian Borch
CB
Frisch
Kim
K
Overgaard
Jacob
J
Jørgensen
Karl Anker
KA
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D002930:Cinchona Alkaloids; D007659:Ketones; D009570:Nitriles; D011809:Quinones