98065-17-9

Upstream product

• 104886-43-3 N-methyl-1-phenylpent-4-en-1-amine 
• 113579-98-9 lithium N-methyl-1-phenylpent-4-enylamide 
• 3240-29-7 1-Phenylpent-4-en-1-one 
• 622-29-7 N-Benzylidenemethylamine 
• 100-52-7 benzaldehyde 
• 113579-81-0 Methyl-[1-phenyl-pent-4-en-(Z)-ylidene]-amine 
• 102632-99-5 1-phenyl-4-penten-1-ol 

Downstream Products

• 113579-89-8 trans-1,1,2-trimethyl-5-phenylpyrrolidinium iodide 
• 113579-89-8 cis-1,1,2-trimethyl-5-phenylpyrrolidinium iodide 
• 104920-99-2 cis-1,1,2-trimethyl-5-phenylpyrrolidinium bromide 
• 104920-99-2 trans-1,1,2-trimethyl-5-phenylpyrrolidinium bromide 

Relevant academic research and scientific papers

New Stereoselective Synthesis of trans-2,5-Disubstituted Pyrrolidines by Cyclization of Aminyl Radicals Generated from 2- and/or 5-Substituted N-Chloro-N-alkylalk-4-enylamines with Bu3SnH-Azoisobutyronitrile

trans-N-Alkyl-2- and/or 5-substituted pyrrolidines are stereoselectively formed in up to 63percent yields by N-chlorination of 2- and/or 5-substituted N-methylpent-4-enylamine with N-chlorosuccinimide, followed by heating a solution of the resulting N-chl

Stereoselective cyclization of δ-alkenylamines catalyzed with butyllithium. Synthesis of cis-N-methyl-2,5-disubstituted pyrrolidines

Treatment of δ-alkenylamines (1a-1d) with a catalytic amount of butyllithium gave cis-N-methyl-2,5-disubstituted pyrrolidines (2a-2d) stereo selectively in good yields.

Control of the Stereoselectivity in the Synthesis of 1-Methyl-2,5-disubstituted Pyrrolidines by Mercury(II)-initiated Cyclization of Substituded Alk-4-enylamines

The stereoselectivity in the synthesis of cis- and trans-1-methyl-2,5-disubstituted pyrrolidines by mercury(II)-initiated cyclization of substituted alk-4-enylamines can be controlled by choosing the appropriate mercury salt and solvent.

CYCLIZATION OF AMINYL RADICALS GENERATED BY ANODIC OXIDATION OF LITHIUM ALKENYLAMIDES. STEREO- AND REGIOSELECTIVE SYNTHESIS OF cis-1-ALKYL-2,5-DISUBSTITUTED PYRROLIDINES

Neutral aminyl radicals (3) generated by anodic oxidation of lithium alkenylamides (2) were found to undergo a stereo- and regioselective cyclization to give cis-1-alkyl-2,5-disubstituted pyrrolidines (5c-5h) in moderate yields.The cis stereochemistry of 5c-5h was confirmed by comparison with the corresponding trans-1-alkyl-2,5-disubstituted pyrrolidines which were prepared by aminomercuration of 1c-1h.The structure of trans-1,2-dimethyl-5-phenylpyrrolidine (17) was established by an X-ray crystallographic analysis of its ammonium bromide 21.Various aminyl radicals examined in this study were found to combine exclusively with the internal carbon of their double bond to give a five- (5a-5h) or six-membered ring (13).No product arising from the cyclization is obtained from N-methyl-1-phenylbut-3-enylamine (14).

AMINYL RADICAL CYCLIZATION BY MEANS OF ANODIC OXIDATION. STEREOSELECTIVE SYNTHESIS OF cis-1-METHYL-2,5-DISUBSTITUED PYRROLIDINES

Neutral aminyl radicals generated by anodic oxidation of lithium alkenylamides 2 undergo a stereoselective cyclization to give cis-1-methyl-2,5-disubstituted pyrrolidines 4.Their cis stereochemistry was confirmed by a comparison with trans-1,2-dimethyl-5-phenylpyrrolidine, the structure of which was established by X-ray crystallographic analysis of its quarternary ammonium bromide 6.