Tetrahedron letters

Aminyl radical cyclization by means of anodic oxidation. Stereoselective synthesis of cis-1-methyl-2, 5-disubstituted pyrrolidines

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

Index: Tokuda, Masao; Yamada, Yasufumi; Takagi, Toshiya; Suginome, Hiroshi; Furusaki, Akio Tetrahedron Letters, 1985 , vol. 26, # 49 p. 6085 - 6088

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Citation Number: 31

Abstract

These alkenylamines were prepared by the Grignard reaction of 4-bromo-1-butene with the appropriate aldehydes, followed by the oxidation of the resulting alcohols with pyridinium chlorochromate to the corresponding ketones, the transformation of the ketones into the N-methylimines, and the reduction of the imines with sodium borohydride. A commercially available 5-hexen-2-one was used for the preparation of 1d. 1a: bp 123–126°C (16 mm Hg); 1b: bp 77–78°C (0.7 ...

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