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 |
|
|