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

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/triethyl‐ amine (5:2, molar ratio), afforded the desired products in good yields (up to 85%) with d...

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Veröffentlicht in:Chinese journal of chemistry 2011-07, Vol.29 (7), p.1467-1472
Hauptverfasser: Wu, Yun, Geng, Zhicong, Bai, Jinjin, Zhang, Yawen
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Sprache:eng
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Zusammenfassung: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/triethyl‐ amine (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. 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), affording 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 product was confirmed by X‐ray crystal structure analysis.
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.201180267