1041403-34-2Relevant academic research and scientific papers
Enantioselective synthesis of tunable chiral clickphine P,N-ligands and their application in Ir-catalyzed asymmetric hydrogenation
Wassenaar, Jeroen,Detz, Remko J.,De Boer, Sandra Y.,Lutz, Martin,Van Maarseveen, Jan H.,Hiemstra, Henk,Reek, Joost N. H.
, p. 3634 - 3642 (2015)
A small library of highly tunable chiral Clickphine P,N-ligands has been prepared in an enantioselective fashion by CuI-catalyzed asymmetric propargylic amination using a single chiral complex and a subsequent in situ cycloaddition click reaction. The scope of the propargylic amination to yield optically active triazolyl amines is described. The amines are transformed in a one-pot procedure to the corresponding Ir-Clickphine complexes, which serve as catalysts for the asymmetric hydrogenation of di-, tri-, and tetrasubstituted unfunctionalized alkenes. Enantioselectivities of up to 90% ee were obtained in these hydrogenations, which are among the best reported in the case of the tetrasubstituted substrate 2-(4′-methoxyphenyl)-3-methylbut-2-ene (9) (87% ee). This is a demonstration of the effective use of the chiral pool, as from one chiral catalyst a library of chiral Ir complexes has been synthesized that can hydrogenate various alkenes with high selectivity.
A hand natural alkyne propyl amine compound catalytic asymmetric synthesis method
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Paragraph 0084; 0085; 0086; 0087, (2018/02/04)
The invention provides a catalytic asymmetric synthesis method of chiral propargyl amine compounds. The catalytic asymmetric synthesis method is characterized by catalyzing asymmetric decarboxylation reactions in molecules of amide propargyl carbonate com
Enantioselective copper-catalyzed propargylic amination
Detz, Remko J.,Delville, Marielle M. E.,Hiemstra, Henk,Van Maarseveen, Jan H.
, p. 3777 - 3780 (2008/12/23)
(Chemical Equation Presented) A proper copper catalyst with a chiral pyridine-2,6-bisoxazoline (pybox) ligand was used to convert a variety of propargylic acetates with aromatic side chains (R = Ar) into their amine counterparts in high yield and with good selectivity (up to 88% ee). The resulting chiral propargylic amines can be elaborated further into P,N ligands (see scheme; DIPEA = diisopropylethylamine).
