587885-44-7

Upstream product

• 90715-73-4 2-(trifluoromethyl)acrylic chloride 
• 2462-34-2 L-valine benzyl ester hydrochloride 
• 21760-98-5 L-valine benzyl ester 

Downstream Products

• 1145789-73-6 benzyl (S)-2-[(S)-2-(benzylaminomethyl)-3,3,3-trifluoropropanoylamino]-3-methylbutanoate 
• 1145789-80-5 benzyl (S)-2-[(S)-2-(dibenzylaminomethyl)-3,3,3-trifluoropropanoylamino]-3-methylbutanoate 

Relevant academic research and scientific papers

The role of fluorine in the stereoselective tandem aza-Michael addition to acrylamide acceptors: An experimental and theoretical mechanistic study

Aza-Michael additions of αamino esters to fluorinated acceptors take place in a highly stereoselective manner, to give partially modified ψNHCH2]retropeptides incorporating a hydrolytically stable trifluoroalanine mimic. The reaction mechanism

Highly stereoselective tandem aza-Michael addition-enolate protonation to form partially modified retropeptide mimetics incorporating a trifluoroalanine surrogate

Fine-tuning of key reaction parameters, such as the solvent and the base used, led to a dramatic improvement in d.r. (from ≈1:1 to 38:1) in a tandem aza-Michael addition-enolate protonation sequence. Thus, the reaction of α-amino ester nucleophiles 1 with N-(α-trifiuoromethyl)acryloyl-α-amino ester acceptors 2 produced an array of partially modified retropeptide mimetics 3 with good to excellent stereocontrol (R, R1, R2, X, X1 = alkyl).