Allyl-2,2,2-trichloroethylamine derivatives 3 were cyclized via dichloromethyl radical to afford selectively cis-2,4-disubstituted pyrrolidine derivatives 4 by the treatment with tributyltin hydride under radical conditions.
Aminyl radical cyclization by means of anodic oxidation. Stereoselective synthesis of cis-1-methyl-2,5-disubstituted pyrrolidines
โ Scribed by Masao Tokuda; Yasufumi Yamada; Toshiya Takagi; Hiroshi Suginome; Akio Furusaki
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 233 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Neutral aminyl radicals generated by anodic oxidation of lithium alkenylamides 2 undergo a stereoselective cyclization to give cis-l-methyl-
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Nitrones were reacted with 3-butenylmagnesium bromide to give alkenylhydroxylamines that were cyclised by retro-Cope elimination. Heating the diastereomeric mixtures of pyrrolidine N-oxides in the absence of solvent affected a highly diastereoselective isomerisation to provide the cis-2,5-disubstitu