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Synthesis of Chiral 2-Aroyl-1-tetralols: Asymmetric Transfer Hydrgenation of 2-Aroyl-1-tetralones via Dynamic Kinetic Resolution

✍ Scribed by Yun Wu; Zhicong Geng; Jinjin Bai; Yawen Zhang

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 96 KB
Volume: 29
Category: Article
ISSN: 0256-7660
DOI: 10.1002/cjoc.201180267

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✦ Synopsis

The dynamic kinetic resolution of 2-aroyl-1-tetralones was achieved via asymmetric transfer hydrogenation using (S,S)-RuCl(p-cymene)TsDPEN (TsDPEN ＝ N-(tosyl)-1,2-diphenylethylenediamine) in formic acid/triethylamine (5∶2, molar ratio), afforded the desired products in good yields (up to 85%) with diastereomeric ratio up to ＞99∶1 and high enantiomeric excesses (up to ＞99%). The absolute configuration of major the product was confirmed by X-ray crystal structure analysis.

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