59759-78-3

Upstream product

• 144754-21-2 2-benzoylamino-3-[1]naphthyl-acrylic acid 
• 495-69-2 Hippuric Acid 
• 66-77-3 1-naphthaldehyde 
• 57427-83-5 4-naphthalen-1-ylmethylene-2-phenyl-4H-oxazol-5-one 
• 59759-53-4 DL-N-Benzoyl-η-1-naphthyl-alaninamid 

Downstream Products

• 141714-02-5 (2R,4S,5S)-N-isobutyl-5--L-norleucyl>amino-2-ethyl-4-hydroxy-7-ethyloctanamide 
• 141714-02-5 (2S,4S,5S)-N-isobutyl-5--L-norleucyl>amino-2-ethyl-4-hydroxy-7-ethyloctanamide 
• 141713-96-4 ((S)-1-{(S)-1-[(1S,2S)-2-Hydroxy-1-isobutyl-4-(2-morpholin-4-yl-ethylcarbamoyl)-hexylcarbamoyl]-pentylcarbamoyl}-2-naphthalen-1-yl-ethyl)-carbamic acid benzyl ester 
• 141714-03-6 (2RS,4S,5S)-N-isobutyl-5--L-norleucyl>amino-2-ethyl-4-hydroxy-6-phenylhexanamide 
• 141713-93-1 (5S,6S)-6-[(S)-2-((S)-2-Benzyloxycarbonylamino-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-5-hydroxy-3-isobutylcarbamoyl-8-methyl-nonanoic acid tert-butyl ester 
• 141713-95-3 [(S)-1-((S)-1-{(1S,2S)-2-Hydroxy-1-isobutyl-4-[(pyridin-4-ylmethyl)-carbamoyl]-hexylcarbamoyl}-pentylcarbamoyl)-2-naphthalen-1-yl-ethyl]-carbamic acid benzyl ester 
• 118586-65-5 {(S)-2-Naphthalen-1-yl-1-[(S)-1-((1S,2S)-2,6,7-trihydroxy-1-isobutyl-4-isobutylcarbamoyl-heptylcarbamoyl)-pentylcarbamoyl]-ethyl}-carbamic acid benzyl ester 
• 141738-66-1 (2RS,4S,5S)-N-isobutyl-5--L-norleucyl>amino-6-cyclohexyl-2-ethyl-4-hydroxyhexanamide 
• 118586-63-3 {(S)-1-[(S)-1-((1S,2S,4R)-2,7-Dihydroxy-1-isobutyl-4-isobutylcarbamoyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 118609-75-9 {(S)-1-[(S)-1-((1S,2S)-2,6-Dihydroxy-1-isobutyl-4-isobutylcarbamoyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 141713-94-2 {(S)-1-[(S)-1-((1S,2S)-7-Amino-2-hydroxy-1-isobutyl-4-isobutylcarbamoyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 118586-64-4 {(S)-1-[(S)-1-((1S,2S,4R)-2,6-Dihydroxy-1-isobutyl-4-isobutylcarbamoyl-hexylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 141713-92-0 {(S)-1-[(S)-1-((1S,2S,4R)-2-Hydroxy-1-isobutyl-4-isobutylcarbamoyl-6-methyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 
• 141713-91-9 {(S)-1-[(S)-1-((1S,2S,4R)-2-Hydroxy-1-isobutyl-4-isobutylcarbamoyl-heptylcarbamoyl)-pentylcarbamoyl]-2-naphthalen-1-yl-ethyl}-carbamic acid benzyl ester 

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′.

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.