113579-83-2

Upstream product

• 26954-35-8 1-(4-methoxyphenyl)pent-4-en-1-one 
• 74-89-5 methylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 113579-77-4 1-(4-methoxy-phenyl)-pent-4-en-1-ol 

Downstream Products

• 104886-48-8 (2S,5R)-2-(4-Methoxy-phenyl)-1,5-dimethyl-pyrrolidine 
• 104886-48-8 cis-1,2-dimethyl-5-(4-methoxyphenyl)pyrrolidine 
• 113580-00-0 lithium N-methyl-1-(4-methoxyphenyl)pent-4-enylamide 
• 104886-45-5 N-methyl-1-(4-methoxyphenyl)pent-4-enylamine 

Relevant academic research and scientific papers

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.