142075-07-8

Upstream product

• 111944-26-4 methyl-N-(4-bromo-4-phenylbutyl)carbamate 
• 250691-28-2 methyl pyrrolidinecarboxylate iminium cation 
• 591-51-5 phenyllithium 
• 17763-67-6 Phenyl triflate 
• 76460-88-3 N-methoxycarbonyl-2,3-dihydropyrrole 
• 1006-64-0 2-(phenyl)pyrrolidine 
• 79-22-1 methyl chloroformate 
• 111944-13-9 methyl N-bromo-N-(4-phenylbutyl)carbamate 
• 56475-80-0 N-(methoxycarbonyl)pyrrolidine 

Downstream Products

• 76403-42-4 2-Oxo-5-phenyl-pyrrolidine-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Electrochemical Functional-Group-Tolerant Shono-type Oxidation of Cyclic Carbamates Enabled by Aminoxyl Mediators

An electrochemical method has been developed for α-oxygenations of cyclic carbamates by using a bicyclic aminoxyl as a mediator and water as the nucleophile. The mediated electrochemical process enables substrate oxygenation to proceed at a potential that is approximately 1 V lower than the redox potential of the carbamate substrate. This feature allows for functional-group compatibility that is inaccessible with conventional Shono oxidations, which proceed by direct electrochemical substrate oxidation. This reaction also represents the first α-functionalization of non-activated cyclic carbamates with oxoammonium oxidants.

Reaction of an electrogenerated 'iminium cation pool' with organometallic reagents. Direct oxidative α-alkylation and -arylation of amine derivatives

We have developed an efficient direct oxidative α-alkylation and -arylation of carbamates based on the 'cation pool' method. Grignard reagents, organozinc compounds, and organoaluminum compounds are effective as carbon nucleophiles toward iminium cation pools generated by low temperature electrolysis of carbamates.

Catalytic asymmetric arylation of N-substituted 2-pyrrolines with aryl triflates

Catalytic asymmetric arylation of 1-(alkoxycarbonyl)-2-pyrrolines (4) with aryl triflates (1) in benzene in the presence of a base and a palladium catalyst, prepared in situ by mixing Pd(OAc)2 and (R)-BINAP, gives optically active (R)-1-(alkoxycarbonyl)5-aryl-2-pyrrolines (5) of up to 83percent ee. together with the regioisomers 1-(alkoxycarbonyl)-5-aryl-3-pyrrolines (6).

REACTIONS OF CARBAMYL RADICALS: INTRAMOLECULAR HYDROGEN ABSTRACTION REACTIONS

ω-Phenylalkyl-N-methylcarbamyl radicals undergo intermolecular addition to 3,3-dimethylbut-1-ene in preference to intramolecular hydrogen abstraction.Methyl N-(ω-phenylalkyl) carbamyl radicals and methyl N-pentylcarbamyl radicals readily abstract hydrogen