221071-23-4Relevant academic research and scientific papers
Dynamic Kinetic Resolution of Azlactones by a Chiral N, N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups
Mandai, Hiroki,Hongo, Kohei,Fujiwara, Takuma,Fujii, Kazuki,Mitsudo, Koichi,Suga, Seiji
, p. 4811 - 4814 (2018/08/24)
A dynamic kinetic resolution (DKR) of azlactones in the presence of benzoic acid and a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1i having two amide groups at the 3,3′-positions of a binaphthyl unit is developed. The reaction proceeded smoothly with a wide range of azlactones to provide α-amino acid derivatives with good to high enantiomeric ratios (er's). A multigram-scale reaction (2.5 g) for the DKR of azlactone 2d was also demonstrated, and the resulting product was converted to unnatural α-amino acid 6d′.
Peptide-catalyzed conversion of racemic oxazol-5(4 H)-ones into enantiomerically enriched α-amino acid derivatives
Metrano, Anthony J.,Miller, Scott J.
, p. 1542 - 1554 (2014/03/21)
We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.
Polyclonal antibodies: A cheap and efficient tool for screening of enantioselective catalysts
MacOvei, Cristian,Vicennati, Paola,Quinton, Julia,Nevers, Marie-Claire,Volland, Herve,Creminon, Christophe,Taran, Frederic
supporting information; experimental part, p. 4411 - 4413 (2012/05/20)
Enantioselective polyclonal antibodies have been produced and characterized to develop a high-throughput screening method for lipase activity fingerprinting, with a view to the enantioselective hydrolysis of azlactones.
Ring opening with kinetic resolution of azlactones by Ti-TADDOLates
Gottwald, Konstanze,Seebach, Dieter
, p. 723 - 738 (2007/10/03)
The kinetic resolution of azlactones by the Lewis, acid-mediated transfer of an isopropoxide ligand from the chiral ligand sphere of Ti- TADDOLate is described. The reactions proceed with in-situ racemization of the starting material to afford highly enantiomerically enriched N-benzoyl- amino acid isopropylesters (er > 95:5 after recrystallization). The absolute configuration of the major enantiomer of N-benzoyl-phenylalanine isopropyl ester and its analogs with other aromatic substituents was shown to be (S)- (+) when the (R,R)-Ti-TADDOLate was employed. Only benzyl-substituted azlactones can be opened enantioselectively by the method described here.
