PMID: 11330896May 2, 2001Paper

Remote dipole effects as a means to accelerate [Ru(amino alcohol)]-catalyzed transfer hydrogenation of ketones

Chemistry : a European Journal
S J NordinP G Andersson

Abstract

A new generation of 2-aza-norbornyl amino alcohol ligands for the catalytic transfer hydrogenation reaction of aromatic ketones was synthesized. Extremely active catalysts were formed by introducing a ketal functionality at the rear end of the ligand. Acetophenone was reduced in 96% ee at low catalyst loading, substrate to catalyst ratio, S/C 5000, within 90 minutes with isopropyl alcohol as the hydrogen donor. It was found that the dioxolane substituent in the ligand increased the turnover frequency, TOF50, from 1050 h(-1) to 3000 h(-1) at an S/C ratio of 1000. Introduction of a methyl group at the carbinol carbon resulted in TOF50 as high as 8500 h(-1). Transfer hydrogenation of a range of aromatic ketones was evaluated and found to reach completion within 30 minutes at room temperature, and excellent enantioselectivity, up to 99 % ee, was obtained. A possible explanation for the enhanced activity was provided by density functional calculations, which showed that the presence of a remote dipole in the ligand lowered the transition state energy.

Citations

May 24, 2011·Journal of the American Chemical Society·Paola RizzoGaetano Guerra
Aug 3, 2011·Journal of the American Chemical Society·Laura M LanniJohn J Lavigne
Jul 8, 2011·Journal of the American Chemical Society·Yoshikazu ItoToshiaki Enoki
Feb 18, 2012·Journal of the American Chemical Society·Martin D DonakowskiKenneth R Poeppelmeier
Oct 27, 2012·Journal of the American Chemical Society·Anne SimoKlaus Rademann
Mar 1, 2006·Chemical Society Reviews·Serafino Gladiali, Elisabetta Alberico
Mar 19, 2008·Angewandte Chemie·Theo ZweifelHansjörg Grützmacher
Oct 11, 2008·Chemistry : a European Journal·Clarite Azerraf, Dmitri Gelman
Aug 20, 2010·Organic & Biomolecular Chemistry·Fredrik Tinnis, Hans Adolfsson
Aug 11, 2005·Chemical Communications : Chem Comm·Patrik VästiläHans Adolfsson
Mar 1, 2006·Chemical Society Reviews·Joseph S M SamecPeter Brandt
Apr 11, 2009·Chemistry : a European Journal·Nils MeyerRobert H Morris
Jun 15, 2007·Chemical Communications : Chem Comm·Xiaofeng Wu, Jianliang Xiao
Nov 30, 2004·Chemical Communications : Chem Comm·Joseph S M SamecJan-E Bäckvall
Feb 14, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Marek KuzmaPetr Kačer
Dec 18, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Manuela Delgado-RebolloMartin Albrecht
Jan 30, 2004·Journal of the American Chemical Society·Jérôme HannedoucheMartin Wills
Sep 10, 2009·Organic Letters·Takeyuki SuzukiHiroaki Sasai
Apr 13, 2005·The Journal of Organic Chemistry·Fung Kei Kathy CheungMartin Wills
Jul 17, 2004·The Journal of Organic Chemistry·Peter BrandtPher G Andersson
Aug 4, 2004·The Journal of Organic Chemistry·Stephanie BastinMartin Wills
Aug 26, 2006·The Journal of Organic Chemistry·David J MorrisMartin Wills

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