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Diastereoselective synthesis of cis-2,5-disubstituted pyrrolidine N-oxides by the retro-Cope elimination

✍ Scribed by Mark C Bagley; Julie Tovey

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 64 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01964-x

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✦ Synopsis

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-disubstituted products in excellent yield.

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