title: Enantioselective construction of 2,3-dihydrofuro[2,3-b]quinolines through supramolecular hydrogen bonding interactions.
abstract: The first asymmetric synthesis of 2,3-dihydrofuro[2,3-b]quinolines has been achieved by a cascade asymmetric aziridination/intramolecular ring-opening process of differently substituted 3-alkenylquinolones. Good yields and high enantioselectivities (up to 78% yield and 95% ee) were recorded when employing 2,2,2-trichloroethoxysulfonamide as the nitrene source, PhI(OCOtBu)2 as the oxidant, and a chiral C2 -symmetric Rh(II) complex as the catalyst (1 mol%). The catalyst bears two lactam motifs, which serve as binding sites for substrate coordination through supramolecular hydrogen-bonding interactions.
authors.affiliation: Lehrstuhl für Organische Chemie I and Catalysis Research Center (CRC), Technische Universität München, Lichtenbergstrasse 4, 85747 Garching (Germany), Fax: (+49) 89-289-13315.
authors.forename: Fangrui
authors.initials: F
authors.lastname: Zhong
authors.forename: Thorsten
authors.initials: T
authors.lastname: Bach
mesh_terms: D001388:Aziridines / Q000737:chemistry; D006860:Hydrogen Bonding; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D011804:Quinolines; D012238:Rhodium
keywords: asymmetric catalysis; enantioselectivity; hydrogen bonding; nitrogen heterocycles; rhodium