title: Combining silver catalysis and organocatalysis: a sequential Michael addition/hydroalkoxylation one-pot approach to annulated coumarins.
abstract: A highly stereoselective one-pot procedure for the synthesis of five-membered annulated hydroxycoumarins has been developed. By merging primary amine catalysis with silver catalysis, a series of functionalized coumarin derivatives were obtained in good yields (up to 91%) and good to excellent enantioselectivities (up to 99% ee) via a Michael addition/hydroalkoxylation reaction. Depending on the substituents on the enynone, the synthesis of annulated six-membered rings is also feasible.
authors.affiliation: Institute of Organic Chemistry, RWTH Aachen University , Landoltweg 1, 52074 Aachen, Germany.
authors.forename: Daniel
authors.initials: D
authors.lastname: Hack
authors.forename: Pankaj
authors.initials: P
authors.lastname: Chauhan
authors.forename: Kristina
authors.initials: K
authors.lastname: Deckers
authors.forename: Gary N
authors.initials: GN
authors.lastname: Hermann
authors.forename: Lucas
authors.initials: L
authors.lastname: Mertens
authors.forename: Gerhard
authors.initials: G
authors.lastname: Raabe
authors.forename: Dieter
authors.initials: D
authors.lastname: Enders
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012834:Silver / Q000737:chemistry*
chemical_list: D000588:Amines; D003374:Coumarins; D012834:Silver