304850-92-8

Upstream product

• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 
• 223595-45-7 (5S)-N-(methoxycarbonyl)-5-(trityloxymethyl)-2-pyrroline 

Downstream Products

• 304850-95-1 (2R,3R,4R,5R)-N-(methoxycarbonyl)-3,4-dihydroxy-5-(methyl)-2-(p-methoxyphenyl)-pyrrolidine 
• 304850-94-0 (2R,3R,4S,5R)-N-(methoxycarbonyl)-3,4-epoxy-5-(methyl)-2-(p-methoxyphenyl)-pyrrolidine 
• 223595-51-5 (2S,5S)-2-Methanesulfonyloxymethyl-5-(4-methoxy-phenyl)-2,5-dihydro-pyrrole-1-carboxylic acid methyl ester 
• 223595-53-7 (2S,5R)-N-(methoxycarbonyl)-5-(methyl)-2-(p-methoxyphenyl)-3-pyrroline 
• 100100-39-8 (R,R,R,R)-N(1)-methyl-2-(4'-methoxyphenyl)-3-hydroxy-4-hydroxy-5-methylpyrroli 
• 534573-29-0 (2R,3R,4R,5R)-3,4-Diacetoxy-2-acetoxymethyl-5-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid methyl ester 
• 534573-28-9 (2R,3R,4R,5R)-3,4-Dihydroxy-2-hydroxymethyl-5-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid methyl ester 
• 223595-49-1 (2S,5S)-N-(methoxycarbonyl)-5-(hydroxymethyl)-2-(p-methoxyphenyl)-3-pyrroline 

Relevant academic research and scientific papers

Probing the stereoselectivity of the Heck arylation of endocyclic enecarbamates with diazonium salts. Concise syntheses of (2S,5R)-phenylproline methyl ester and Schramm's C-azanucleoside.

[reaction: see text] The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coor

Synthesis of dihydroxylated prolines and iminocyclitols from five-membered endocyclic enecarbamates. Total synthesis of the potent glycosidase inhibitor (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine (DMDP)

cis- and trans-3,4-Dihydroxylated prolines and the iminocyclitol 1,4-dideoxy-1,4-imino ribitol were synthesized employing a strategy involving the Heck arylation of five-membered endocyclic enecarbamates with aryldiazonium salts followed by oxidative cleavage of the electron-rich aromatic ring. The total synthesis of the potent α- and β-glucosidase inhibitor (2R,3R,4R,5R)-2,5-hydroxymethyl-3,4-dihydroxypyrrolidine (DMDP) was also achieved by the same strategy in ten steps from a chiral five-membered enecarbamate in 12% overall yield.

Heck arylation of endocyclic enecarbamates with diazonium salts. Improvements and a concise enantioselective synthesis of (-)-codonopsinine.

Total enantioselective synthesis of the natural (-)-codonopsinine was accomplished in seven steps with an overall yield of approximately 16% starting from the five-membered endocyclic enecarbamate 4. The total synthesis features a highly efficient and ste