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Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of aromatic ketones in water using novel water-soluble chiral monosulfonamide ligands

✍ Scribed by Zhongqiang Zhou; Qiong Ma; Yong Sun; Aiqing Zhang; Lin Li

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
147 KB
Volume
21
Category
Article
ISSN
1042-7163

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✦ Synopsis

Abstract

Novel water‐soluble analogues of Noyori's (R,R)‐N‐(p‐tolylsulfonyl)‐1,2‐diphenylethyl‐ enediamine and Knochel's (R,R)‐N‐(p‐tolylsulfonyl)‐1,2‐diaminocyclohexane, containing an additional quaternary ammonium group, have been synthesized. The ruthenium catalysts prepared in situ by reacting chiral monosulfonamides with [RuCl~2~(p‐cymene)]~2~ afforded high conversion rates and enantiomeric excess (ee) values in the asymmetric transfer hydrogenation of aromatic ketones in aqueous HCOONa. Furthermore, the catalyst could be easily recovered and reused at least five times without obvious loss of ee value. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:505–514, 2010; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20641

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Chiral amino amides for the ruthenium(II
Chiral amino amides for the ruthenium(II)-catalyzed asymmetric transfer hydrogenation reaction of ketones in water
✍ Jincheng Mao; Jun Guo 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 119 KB 👁 2 views

## Abstract The chiral amino amide **3** was derived from L‐proline and used for the [RuCl~2~(__p__‐cymene)]~2~‐catalyzed asymmetric transfer hydrogenation of prochiral ketones performed in water. Moderate to good chemical selectivities (up to 95% yield) and enantioselectivities (up to 90% ee) were