Tetrahedron

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

…, Y Yamada, T Takagi, H Suginome, A Furusaki

Index: Tokuda, Masao; Yamada, Yasufumi; Takagi, Toshiya; Suginome, Hiroshi; Furusaki, Akio Tetrahedron, 1987 , vol. 43, # 2 p. 281 - 296

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Citation Number: 53

Abstract

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- ...