CeCl3.7H2O: an effective additive in Ru-catalyzed enantioselective hydrogenation of aromatic alpha-ketoesters

The Journal of Organic Chemistry
Qinghua MengZhaoguo Zhang

Abstract

In the presence of catalytic amounts of CeCl 3.7H 2O, [RuCl(benzene)(S)-SunPhos]Cl is a highly effective catalyst for the asymmetric hydrogenation of aromatic alpha-ketoesters. A variety of ethyl alpha-hydroxy-alpha-arylacetates have been prepared in up to 98.3% ee with a TON up to 10,000. Challenging aromatic alpha-ketoesters with ortho substituents are also hydrogenated with high enantioselectivities. The addition of CeCl 3.7H 2O not only improves the enantioselectivity but also enhances the stability of the catalyst. The ratio of CeCl 3.7H 2O to [RuCl(benzene)(S)-SunPhos]Cl plays an important role in the hydrogenation reaction with a large substrate/catalyst ratio.

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Citations

Dec 19, 2012·The Journal of Organic Chemistry·Alison E Metz, Marisa C Kozlowski
Feb 3, 2012·Chemical Communications : Chem Comm·Yasunori YamamotoNorio Miyaura
Mar 20, 2014·Chemical Communications : Chem Comm·Dieter EndersAndreas Rembiak
Feb 10, 2012·Chemical Society Reviews·David J AgerJohannes G de Vries
May 31, 2013·Organic & Biomolecular Chemistry·Jia-Fei PoonPeter Dinér
Jul 8, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Wanfang LiZhaoguo Zhang
Aug 8, 2009·The Journal of Organic Chemistry·Zhi-Yong PengZhaoguo Zhang
Aug 13, 2010·The Journal of Organic Chemistry·Lvfeng ZhuZhaoguo Zhang
Aug 25, 2010·Chemical Reviews·Giuseppe BartoliLetizia Sambri
Nov 24, 2011·The Journal of Organic Chemistry·Xiaoming TaoZhaoguo Zhang
Oct 11, 2011·The Journal of Organic Chemistry·Weizheng FanZhaoguo Zhang
Sep 11, 2012·The Journal of Organic Chemistry·Xiaoming TaoZhaoguo Zhang
Jun 17, 2014·The Journal of Organic Chemistry·Mengmeng ZhaoZhaoguo Zhang
Jul 25, 2012·Organic Letters·Olivier JackowskiVirginie Ratovelomanana-Vidal
Dec 31, 2021·Organic Letters·Jacob G Robins, Jeffrey S Johnson

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