PMID: 11322546Apr 27, 2001Paper

Solid-phase synthesis of homogeneous ruthenium catalysts on silica for the continuous asymmetric transfer hydrogenation reaction

Chemistry : a European Journal
A J SandeeP W van Leeuwen

Abstract

The solid-phase synthesis of new asymmetric transfer hydrogenation catalysts as well as the use of these silica supported systems in batch and flow reactors is reported. The ruthenium complex of NH-benzyl-(1R,2S)-(-)-norephedrine covalently tethered to silica showed a high activity and enantioselectivity in the reduction of acetophenone. In three consecutive batchwise catalytic runs, we obtained ee values of 88%. In a continuous flow reactor, a very constant catalytic activity was observed; no catalyst deactivation occurred over a period of one week. This has been ascribed to successful site isolation. Using optimized conditions in this flow reactor, the ee was as high as 90% at 95% conversion. The supported catalysts generally show the same trend in catalyst performance as in solution. The viability of our approach was further shown in one example, the ruthenium(II) complex of (1S,2R)-(+)-2-amino-1,2-diphenylethanol, for which an enantiomeric excess of 58% was observed, which is nearly three times higher than its homogeneous analogue.

Citations

Mar 26, 2013·Journal of the American Chemical Society·Songsu KangChristopher W Bielawski
Nov 7, 2009·Journal of the American Chemical Society·Huanli DongXiong Gong
Aug 5, 2008·Drug Discovery Today·Matteo Colombo, Ilaria Peretto
May 30, 2009·Beilstein Journal of Organic Chemistry·Xiao Yin MakPeter H Seeberger
Jan 8, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Alexander M KluwerJoost N H Reek
Jul 13, 2006·Chemistry : a European Journal·Andreas KirschningKlaas Mennecke
Jun 25, 2005·Organic & Biomolecular Chemistry·Matthew J WilkinsonJoost N H Reek
Oct 10, 2002·Chemical Reviews·Qing-Hua FanAlbert S C Chan
Oct 10, 2002·Chemical Reviews·Choong Eui Song, Sang-Gi Lee
Oct 10, 2002·Chemical Reviews·Zhong-Lin LuHermann A Mayer
Oct 10, 2002·Chemical Reviews·Avelino Corma, Hermenegildo García
Mar 22, 2007·Chemical Reviews·Brian P MasonD Tyler McQuade
Aug 4, 2004·The Journal of Organic Chemistry·Stephanie BastinMartin Wills

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