183874-52-4

Upstream product

• 171038-43-0 ethyl (2S,4R)-N-BOC-4-benzylprolinate 

Downstream Products

• 170947-88-3 ethyl (4R)-N-(methoxycarbonyl)-4-benzyl-2,3-didehydroprolinate 
• 170947-89-4 diethyl <(2R,3S,4R)-N-(methoxycarbonyl)-4-benzyl-2-(ethoxycarbonyl)pyrrolidin-3-yl>malonate 
• 183874-63-7 (2R,3R,4R)-4-Benzyl-3-methyl-pyrrolidine-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester 
• 183874-54-6 (1R,4R,5R)-4-Benzyl-2-aza-bicyclo[3.1.0]hexane-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester 
• 183874-64-8 (2R,3S,4R)-4-Benzyl-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester 
• 183874-60-4 (2R,3S,4R)-4-Benzyl-3-(1-ethoxycarbonyl-2-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester 
• 183874-62-6 (2R,3R,4R)-4-Benzyl-3-(methoxycarbonyl-phenylsulfanyl-methyl)-pyrrolidine-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester 
• 183874-61-5 (2R,3R,4R)-3-(Benzenesulfonyl-methoxycarbonyl-methyl)-4-benzyl-pyrrolidine-1,2-dicarboxylic acid 2-ethyl ester 1-methyl ester 

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.

New enantioselective approach to α-allokainoids by Michael addition to chiral 4-substituted 2,3-didehydroprolinate

(-) and (+) α-Allokainoids hydrochlorides 3 and 4 were obtained by hydrolysis of the corresponding Michael adducts resulting from the addition of diethyl malonate to chiral N-urethane protected ethyl 4-benzyl-2,3-didehydroprolinates 9 and 13 respectively.