199107-84-1Relevant academic research and scientific papers
First Iridium-Catalyzed Highly Enantioselective Hydrogenation of β-Nitroacrylates
Li, Shengkun,Xiao, Taifeng,Li, Dangdang,Zhang, Xumu
, p. 3782 - 3785 (2015/08/18)
The first highly chemo- and enantioselective hydrogenation of β-nitroacrylates was accomplished with an iridium catalyst (Ir-4) with yields and enantioselectivities of up to 96% and 98% ee, respectively. The resulting α-chiral β-nitro propionates are attractive building blocks for the synthesis of chiral β2-amino acids, which are the core scaffolds of bioactive natural products, pharmaceuticals, and β-peptides.
β-Nitro substituted carboxylic acids and their cytotoxicity
Csuk, René,Heller, Lucie,Siewert, Bianka,Gutnov, Andrey,Seidelmann, Oliver,Wendisch, Volkmar
, p. 4011 - 4013 (2014/09/03)
β-Nitro-substituted ethyl carboxylates are a new class of cytotoxic agents; they can be easily obtained in fair to good yields in a single-step reaction by a Pd-catalyzed asymmetric conjugate addition of aryl boronic acids to 2-nitro-acrylates. Of all the tested derivatives, 2-(4-chlorophenyl)-3- nitropropionic acid ethyl ester (6) is most cytotoxic especially against the human ovarian cancer cell line A2780 therefore making this compound an interesting candidate for further investigations.
Pd-catalyzed asymmetric conjugate addition of arylboronic acids to 2-nitroacrylates: A facile route to β2-homophenylglycines
Petri, Andreas,Seidelmann, Oliver,Eilitz, Uwe,Le?mann, Frank,Rei?mann, Stefan,Wendisch, Volkmar,Gutnov, Andrey
, p. 267 - 270 (2014/01/06)
Asymmetric conjugate addition of arylboronic acids to 2-nitroacrylamide in the presence of cationic palladium-Chiraphos complex proceeds with high yield and enantioselectivity (73-89% ee) using as low as 0.05-0.25 mol % of the catalyst. The adducts can be smoothly transformed into the corresponding β2-homophenylglycines in two simple steps.
Stereoselective synthesis of densely functionalized pyrrolidin-2-ones by a conjugate addition/nitro-mannich/lactamization reaction
Anderson, James C.,Horsfall, Lisa R.,Kalogirou, Andreas S.,Mills, Matthew R.,Stepney, Gregory J.,Tizzard, Graham J.
experimental part, p. 6186 - 6198 (2012/09/25)
Copper-catalyzed conjugate addition of diorgano zinc reagents to nitroacrylate 1 followed by a subsequent nitro-Mannich reaction and in situ lactamization leads to an efficient one-pot synthesis of 1,3,5-trisubstituted 4-nitropyrrolidin-2-ones (5). The versatility of the reaction is shown for a wide range of N-p-(methoxy)phenyl protected aldimines 3 derived from alkyl, aryl, and heteroaryl aldehydes. The densely functionalized pyrrolidin-2-ones 5 are isolated as single diastereoisomers (40 examples, 33-84% yield). An enantioselective copper-catalyzed conjugate addition of diethylzinc led to highly crystalline products that could be recrystallized to enantiopurity in high yield. A range of successful chemoselective transformations were investigated, which widens the applicability of the pyrrolidn-2-ones as stereochemically pure building blocks for further organic synthesis.
Readily available hydrogen bond catalysts for the asymmetric transfer hydrogenation of nitroolefins
Schneider, Jakob F.,Lauber, Markus B.,Muhr, Vanessa,Kratzer, Domenic,Paradies, Jan
, p. 4323 - 4327 (2011/07/08)
This paper focuses on readily accessible thiourea hydrogen bond catalysts derived from amino acids, whose steric and electronic features are modulated by their degree of substitution at the carbinol carbon center. These catalysts were applied in the asymmetric transfer hydrogenation of nitroolefins furnishing the chiral products in up to 99% yield and 86% enantiomeric excess. The proposed catalyst's mode of action is supported by mechanistic investigations.
