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A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone

✍ Scribed by Alberto Brandi; Stefano Cicchi; Valentina Paschetta; Domingo Gomez Pardo; Janine Cossy

Publisher: Elsevier Science
Year: 2002
Tongue: French
Weight: 106 KB
Volume: 43
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(02)02336-5

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✦ Synopsis

The oxidation of a C 2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, is reported. Oxidation with C-phenyl-N-phenylsulfonyloxaziridine afforded the corresponding nitrone that is too unstable for isolation and which reacted in situ with dimethyl maleate. The major adduct was transformed to the corresponding protected dihydroxyindolizidinone.

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