193468-18-7

Upstream product

• 616-02-4 citraconic acid anhydride 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 193468-16-5 (2Z)-(+)-ethyl 2-methyl-3-[(S)-α-methylbenzylamino]-2-butenoate 

Relevant academic research and scientific papers

Enantioselective access to five- and six-membered nitrogen-containing heterocycles, based on the asymmetric michael addition of chiral imines and chiral enamino esters

The addition reaction of chiral imines, (ent-10, 48, 70) and chiral enamino esters (52, 55, 73) with maleic anhydride (32), citraconic anhydride (57), α-chloroacrylonitrile (29), and nitroethylene (74), has been investigated. These condensations proved to be in general highly regio-, diastereo-, and enantioselective. In most cases the primary adducts underwent an in situ N-heterocyclization, allowing the enantioselective access to nitrogen-containing, five-and six-membered heterocycles.

Condensation of chiral imines and chiral β-enaminoesters with maleic and citraconic anhydrides

Condensations of chiral imines 1 and 4, and chiral enaminoesters 10 and 13, with maleic and citraconic anhydrides were reported. These experimental outcomes can be rationalized by invoking the compact, endo-approaches of the two reactions 18.