183874-63-7

Upstream product

• 171038-43-0 ethyl (2S,4R)-N-BOC-4-benzylprolinate 
• 183874-52-4 ethyl (4R)-4-benzylpyrroline-2-carboxylate 
• 917-54-4 methyllithium 
• 170947-88-3 ethyl (4R)-N-(methoxycarbonyl)-4-benzyl-2,3-didehydroprolinate 

Relevant academic research and scientific papers

4-Benzyl-2,3-didehydroprolinate as a homochiral template for Michael additions. Synthesis of enantiopure α-allokainoids, β-kainoids, 2,3-methanoprolines and other 3,4-disubstituted prolines

Ethyl (4R)-N-methoxycarbonyl-4-benzyl-2,3-didehydroprolinate 10a undergoes Michael additions with stabilized carbanions and cuprates giving exclusively the enantiopure all-trans 3,4-disubstituted prolinates. The high stereoselection observed in this reaction is driven by the C-4 substituent of the Michael acceptor. This methodology has been applied to the synthesis of the enantiopure β-kainoid 5a and the 2,3-methanoproline 15.