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Updated: Apr 24, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Enantioselective construction of 2,3-dihydrofuro[2,3-b]quinolines through supramolecular hydrogen bonding
1Lehrstuhl für Organische Chemie I and Catalysis Research Center (CRC), Technische Universität 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 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.
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