Remote control by protecting groups in the diastereoselective addition of acetylides to 2-(4-quinolyl)propanol |
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| Affiliation: | 1. School of Materials Science and Engineering, Dalian University of Technology, Dalian, 116024, PR China;2. School of Aeronautics and Astronautics, Faculty of Vehicle Engineering and Mechanics, State Key Laboratory of Structural Analysis for Industrial Equipment, Dalian University of Technology, Dalian 116024, PR China |
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| Abstract: | Differently O-protected 2-(4-quinolyl)propanols undergo, in the presence of chloroformate esters, a regio- and stereoselective addition of acetylides on the carbon α to nitrogen with moderate to good diastereoselectivity. The bulkiness of the OH protecting group, which has a 1,7 relationship with the newly created stereocentre, appears to be mainly responsible for this remote stereocontrol. |
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