861145-13-3

Upstream product

• 1027981-43-6 (2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid 
• 186581-53-3 diazomethane 
• 861145-08-6 (6S,3aR,6aS,S_R)-6-(4-methoxyphenyl)-3-methyl-5-(toluene-4-sulfinyl)-hexahydro-furo[3,4-c]pyrrol-1-one 
• 861145-12-2 (2S,3S,4R,S_R)-[4-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde 
• 861145-04-2 (2S,3S,S_R)-2-(4-methoxyphenyl)-4-methylene-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide 
• 861145-06-4 (2S,3S,4R,S_R)-4-formyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide 
• 861145-05-3 (2S,3S,4R,S_R)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide 
• 861145-07-5 (2S,3S,4R,S_R)-4-(1-hydroxyethyl)-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide 
• 929274-19-1 (R)-(-)-N-(4-methoxybenzylidene)-p-toluenesulfonamide 
• 911028-87-0 (2R,3R)-2-phenyl-3-[(E)-2-phenyl-1-ethenyl]-1-tosylaziridine 
• 1315306-89-8 1-(1-[(4-methylphenyl)sulfonyl]-5-phenyl-4-[(E)-2-phenylethen-1-yl]tetrahydro-1H-pyrrol-3-yl)-1-ethanone 
• 1315306-98-9 (1S,3aR,4S,7aS)-4-methyl-2-[(4-methylphenyl)sulfonyl]-1,6-diphenylperhydropyrano[3,4-c]pyrrol-4-ol 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 137845-37-5 4-methyl-N-(3-phenylallylidene)benzenesulfonamide 

Downstream Products

• 150674-69-4 methyl [2S-(2α,3β,4β)]-[2-(methoxycarbonyl)-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate 
• 487-79-6 (-)-kainic acid 
• 301832-55-3 (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

Palladium-mediated annulation of vinyl aziridines with michael acceptors: Stereocontrolled synthesis of substituted pyrrolidines and its application in a formal synthesis of (-)-α-kainic acid

Just add salt: Vinyl aziridines have been treated with methyl vinyl ketone or ethyl thioacrylate in the presence of Pd0 to give pyrrolidines with moderate to good diastereoselectivity. The presence of nBu4NCl was critical to successf

Total synthesis of (-)-(α)-kainic acid via a diastereoselective methylenecyclopropane ring expansion

(Chemical Equation Presented) A concise and enantioselective synthesis of (-)-(α)-kainic acid in 13 steps with an overall yield of 15% is reported. The pyrrolidine kainoid precursor with the required C2/C3 trans stereochemistry was prepared with excellent diastereoselectivity (>20:1) via a Mgl 2-mediated ring expansion of a tertiary methylenecyclopropyl amide. A selective hydroboration was then employed to set the remaining stereochemistry at the C4 position en route to (-)-(α)-kainic acid.