69935-10-0

Upstream product

• 68100-05-0 2-phenyl-4-(thiophen-2-ylmethylidene)-1,3-oxazol-5(4 H)-one 
• 495-69-2 Hippuric Acid 
• 221071-23-4 2-phenyl-4-(thiophen-2-ylmethyl)oxazol-5(4H)-one 
• 98-88-4 benzoyl chloride 
• 2021-58-1 rac-3-(2-thienyl)alanine 

Downstream Products

• 848674-99-7 2-benzoyl(prop-2-ynyl)amino-2-(thien-2-yl)methylpenta-3,4-dienoic acid methyl ester 
• 848675-10-5 2-benzoylamino-2-(thien-2-yl)methylpenta-3,4-dienoic acid methyl ester 
• 848675-09-2 2-benzoylamino-3-(thien-2-yl)propionic acid prop-2-ynyl ester 
• 221071-23-4 2-phenyl-4-(thiophen-2-ylmethyl)oxazol-5(4H)-one 

Relevant 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

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′.

Polyclonal antibodies: A cheap and efficient tool for screening of enantioselective catalysts

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

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.