223595-44-6

Upstream product

• 98-79-3 L-Pyroglutamic acid 
• 245674-31-1 (5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone 
• 132974-83-5 (5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one 

Downstream Products

• 223595-51-5 (2S,5S)-2-Methanesulfonyloxymethyl-5-(4-methoxy-phenyl)-2,5-dihydro-pyrrole-1-carboxylic acid methyl ester 
• 223595-54-8 (1S,2R,4R,5R)-2-Hydroxymethyl-4-(4-methoxy-phenyl)-6-oxa-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid methyl ester 
• 223595-43-5 (2R,3R,4R,5R)-2-(hydroxymethyl)-5-(4-methoxyphenyl)pyrrolidine-3,4-diol 
• 223595-49-1 (2S,5S)-N-(methoxycarbonyl)-5-(hydroxymethyl)-2-(p-methoxyphenyl)-3-pyrroline 
• 223595-53-7 (2S,5R)-N-(methoxycarbonyl)-5-(methyl)-2-(p-methoxyphenyl)-3-pyrroline 
• 223595-46-8 (2S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-phenyl)-2,5-dihydro-pyrrole-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Efficient and Expeditious Protocols for the Synthesis of Racemic and Enantiomerically Pure Endocyclic Enecarbamates from N-Acyl Lactams and N-Acyl Pyrrolidines

A mild, practical, and straightforward protocol for the construction of endocyclic enecarbamates starting from N-acyl lactams and N-acyl pyrrolidines is presented. Lactams were reduced to the corresponding α-hydroxycarbamates in good to excellent yields using DIBAL-H, SuperHydride, or NaBH4 followed by β-elimination (dehydration) promoted by trifluoroacetic anhydride in the presence of hindered nitrogenated bases such as 2,6-lutidine, diisopropylethylamine, or triethylamine. Small variations of this protocol permitted the preparation of several endocyclic enecarbamates (12 examples) in good to excellent overall yields (56-96%). The protocol was demonstrated to be applicable to several ring sizes, compatible with different protecting groups, and to be mild enough to prevent racemization of racemization-prone stereocenters. The efficacy of the procedure in the preparation of enantiomerically pure endocyclic enecarbamates was also demonstrated and compared to the commonly used Shono's protocol, which in our hands led to partial racemization of the endocyclic enecarbamate 18c.

Heck reaction of endocyclic enecarbemates with diazonium salts. Formal enantioselective syntheses of alkaloids (-)-codonopsine and (-)- codonopsinine, and the synthesis of a new C-aryl azasugar

Formal total syntheses of the pyrrolidine alkaloids (-)-codonopsine and (-)-codonopsinine, as well as the synthesis of a new C-aryl azasugar were accomplished from a common 5-membered, enantiomerically pure endocyclic enecarbamate. The key step in those s