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Enantioselective Construction of 2,3‐Dihydrofuro[2,3‐b]quinolines through Supramolecular Hydrogen Bonding Interactions
Authors:Dr. Fangrui Zhong  Prof. Dr. Thorsten Bach
Affiliation:Lehrstuhl für Organische Chemie I and Catalysis Research Center (CRC), Technische Universit?t München, Lichtenbergstrasse 4, 85747 Garching (Germany), Fax: (+49)?89‐289‐13315
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 RhII 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.
Keywords:asymmetric catalysis  enantioselectivity  hydrogen bonding  nitrogen heterocycles  rhodium
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