The importance of the N-H bond in Ru/TsDPEN complexes for asymmetric transfer hydrogenation of ketones and imines.
نویسندگان
چکیده
Ru(II) complexes of TsDPEN containing two alkyl groups on the non-tosylated nitrogen atom are poor catalysts for asymmetric transfer hydrogenation of ketones and imines; this observation provides direct evidence for the importance of the N-H interaction in the transition state for ketone reduction.
منابع مشابه
Asymmetric transfer hydrogenation over Ru-TsDPEN catalysts supported on siliceous mesocellular foam.
A siliceous mesocellular foam-immobilized Ru-TsDPEN complex exhibited excellent catalytic reactivity, enantioselectivity and reusability in the asymmetric transfer hydrogenation of an imine and ketones.
متن کاملBifunctional transition metal-based molecular catalysts for asymmetric syntheses.
The discovery and development of conceptually new chiral bifunctional transition metal-based catalysts for asymmetric reactions is described. The chiral bifunctional Ru catalyst was originally developed for asymmetric transfer hydrogenation of ketones and imines and is now successfully applicable to enantioselective C-C bond formation reaction with a wide scope and high practicability. The depr...
متن کاملThe Development of Phosphine-Free "Tethered" Ruthenium(II) Catalysts for the Asymmetric Reduction of Ketones and Imines.
In this account, we describe the design, synthesis and applications of tethered versions of the Ru(II)/N-tosyl-1,2-diphenylethylene-1,2-diamine (TsDPEN) class of catalyst that are commonly used for asymmetric transfer hydrogenation and asymmetric hydrogenation of ketones and imines. The review covers key aspects of the reaction mechanisms and examples of applications, including industrial appli...
متن کاملAsymmetric transfer hydrogenation of imines and ketones using chiral Ru(II)Cl(η6-p-cymene)[(S,S)-N-TsDPEN] catalyst: a computational study
Noyori et al. in 1996 showed that the Ru(II)Cl(h-pcymene)[N-p-tosyl-1,2-diphenylethylenediamine] (= [RuCl(h-p-cymene)TsDPEN]) in a HCOOH / triethylamine (TEA) mixture was able to efficiently hydrogenate substituted isoquinolines with high enantioselectivity (asymmetric transfer hydrogenation (ATH)) [1]. Almost simultaneously, the same system was reported to reduce ketones superbly by Fujii et a...
متن کاملOpportunities offered by chiral η⁶-arene/N-arylsulfonyl-diamine-RuII catalysts in the asymmetric transfer hydrogenation of ketones and imines.
Methods for the asymmetric transfer hydrogenation (ATH) of ketones and imines are still being intensively studied and developed. Of foremost interest is the use of Noyori's [RuCl(η⁶-arene)(N-TsDPEN)] complexes in the presence of a hydrogen donor (i-PrOH, formic acid). These complexes have found numerous practical applications and have been extensively modified. The resulting derivatives have be...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 9 9 شماره
صفحات -
تاریخ انتشار 2011