87726-81-6

Upstream product

• 687-47-8 (S)-Ethyl lactate 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 63696-99-1 (S)-ethyl 2-(methylsulfonyloxy)propanoate 
• 84028-88-6 ethyl (S)-lactate triflate 
• 535-11-5 Ethyl 2-bromopropionate 

Downstream Products

• 188822-66-4 (S)-2-[(2-Chloro-acetyl)-((S)-1-phenyl-ethyl)-amino]-propionic acid ethyl ester 
• 188822-70-0 (S)-5-Ethoxy-6-methyl-1-((S)-1-phenyl-ethyl)-3,6-dihydro-1H-pyrazin-2-one 
• 188822-68-6 (6S,1'S)-1-(1'-phenethyl)-6-methyl-piperazine-2,5-dione 

Relevant academic research and scientific papers

Stereoselective synthesis of dipeptides - I

The alkylation of 7 occurs in moderate to good trans stereoselection (d.e.40-98%), while a poorer d.e. (40-98%) is observed for 8. On the contrary, in both substrates the alkylation with CH3I produces a greater amount of the cis isomer (d.e.48%).). Cleavage of the lactims 9(a,e) gives enantiomerically pure dipeptides 14(a,e). The absolute configuration of the introduced stereogenic centres has been assigned on the basis of the 1H-NMR data in connection with the conformational analysis.

Amino Acids, 4 - Enantioselective Synthesis of N-Substituted α-Amino Carboxylic Acids from α-Hydroxy Carboxylic Acids

With primary and secondary amines, the (S)-α-(trifluoromethylsulfonyloxy) carboxylates (S)-3 afford in an SN2 reaction the N-substituted (R)-α-amino carboxylates (R)-5, (R)-9, and (R)-12, resp.The rates of α-substituted ethyl propionates decrease in the order of the substituents triflate (3a) >> bromide (8a) > mesylate (7a) >= tosylate (7b) > chloride (8b); in the reactions with amines, decreasing reactivity affords increasing racemisation and elimination as a consequence of the more drastic conditions which are required