Cyclization of aminyl radicals generated by anodic oxidation of lithium alkenylamides. Stereo- and regioselective synthesis of cis-l-alkyl-2, 5-disubstituted pyrrolidines

Autor:	Akio Furusaki, Yasufumi Yamada, Hiroshi Suginome, Masao Tokuda, Toshiya Takagi
Rok vydání:	1987
Předmět:	chemistry.chemical_classification Ammonium bromide Double bond Stereochemistry Radical Organic Chemistry Regioselectivity chemistry.chemical_element Biochemistry Medicinal chemistry Lithium perchlorate chemistry.chemical_compound chemistry Drug Discovery Stereoselectivity Lithium Alkyl
Zdroj:	Tetrahedron. 43:281-296
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(01)89956-7
Popis:	Neutral aminyl radicals (3) generated by anodic oxidation of lithium alkenylanides (2) were found to undergo a stereo- and regioaelective cyclization to give cis -1-alkyl-2, 5-disubatituted pyrrolidines (5c–5h) in moderate yields. The cis stereochemistry of 5c–5h was confirmed by comparison with the corresponding trans -1-allkyl-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–5l) or six-membered ring (13). No product arising from the cyclization is obtained from N-methyl-1-phenylbut-3-enylamine (14).
Databáze:	OpenAIRE
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