86169-29-1Relevant academic research and scientific papers
Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system
Yang, Yihua,Liu, Shouxin,Li, Junzhang,Tian, Xia,Zhen, Xiaoli,Han, Jianrong
experimental part, p. 2540 - 2554 (2012/07/27)
(Chemical Equation Presented) A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. Copyright Taylor & Francis Group, LLC.
Efficient ligand-free, palladium-catalyzed amidocarbonylation in ionic liquids: Facile synthesis of N-acyl-α-arylglycines
Zhao, Qing-Lu,Yang, Min,Wang, Lai-Lai
experimental part, p. 4460 - 4473 (2009/04/07)
A ligand-free, palladium-catalyzed amidocarbonylation reaction of aromatic aldehyde, acetamide, and CO in ionic liquids [C4mim]PF6, [C6mim]PF6, [C8mim]PF6, and [C6mim]BF4 as solvents is developed. The yields decreased in the order [C6mim]PF6 > [C8mim]PF6 > [C4mim]PF6 > [C6mim]BF4, and substrate concentration affected the catalytic activity of amidocarbonylation. The excellent yield with up to 98% in amidocarbonylation of benzaldehyde was obtained using 15 mol% LiBr · H2O and 6 mol% H2SO4 at 80°C. This reaction could proceed smoothly, resulting in several functionalized ortho-, meta-, and para-substituted N-acyl-α-phenylglycines in moderate to good yields, and o-tolualdehyde and m-tolualdehyde as substrates were amidocarbonylated for the first time in [C6mim]PF6. A significant dependence of product yield on both substituent position and electronic effect of aromatic aldehyde was observed. The ligand-free synthetic method and convenient separation of the products highlighted the versatility of this newly developed methodology. Copyright Taylor & Francis Group, LLC.
Efficient chemoenzymatic synthesis of enantiomerically pure α-amino acids
Beller, Matthias,Eckert, Markus,Geissler, Holger,Napierski, Bernd,Rebenstock, Heinz-Peter,Holla, E. Wolfgang
, p. 935 - 941 (2007/10/03)
A general two-step chemoenzymatic synthesis for enantiomerically pure natural and nonnatural α-amino acids is presented. In the first step of the sequence, the ubiquitous educts aldehyde, amide and carbon monoxide react by palladium-catalyzed amidocarbonylation to afford the racemic N-acyl amino acids in excellent yields. In the second step, enzymatic enantioselective hydrolysis yields the free optically pure a-amino acid and the other enantiomer as the N-acyl derivative, both in optical purities of 85-99.5% ee. The advantage of the chemoenzymatic process compared to other amino acid synthesis are demonstrated by the preparation of various functionalized (-OR, -Cl, -F, -SR) α-amino acids on a 10-g scale.
