The oxidation of a C2 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.
A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone / A. Brandi; S. Cicchi; V. Paschetta; D. Gomez Pardob; J. Cossy. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 43:(2002), pp. 9357-9359. [10.1016/S0040-4039(02)02336-5]
A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone
BRANDI, ALBERTO;CICCHI, STEFANO;
2002
Abstract
The oxidation of a C2 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.File | Dimensione | Formato | |
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