Chiral 3,4-dibenzyloxy-5-hydroxymethyl-2-thiazolylpyrrolidines under Mitsunobu conditions afforded the corresponding R-protected pyrrolidines and 2-deoxy-piperidines in different ratios depending on the stereochemistry of the starting pyrrolidine and the nature of the acid R-OH. A mechanistic scheme is proposed involving the formation of an aziridinium ion as an intermediate.

Ring Enlargement of polyhydroxylated pyrrolidines to piperidines by Mitsunobu reaction: A fortuitous synthesis of 1-Deoxy-L-Allonojirimicina / A. DONDONI; B. RICHICHI; A. MARRA; D. PERRONE. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - 10:(2004), pp. 1711-1714. [10.1055/s-2004-829566]

Ring Enlargement of polyhydroxylated pyrrolidines to piperidines by Mitsunobu reaction: A fortuitous synthesis of 1-Deoxy-L-Allonojirimicina

RICHICHI, BARBARA;
2004

Abstract

Chiral 3,4-dibenzyloxy-5-hydroxymethyl-2-thiazolylpyrrolidines under Mitsunobu conditions afforded the corresponding R-protected pyrrolidines and 2-deoxy-piperidines in different ratios depending on the stereochemistry of the starting pyrrolidine and the nature of the acid R-OH. A mechanistic scheme is proposed involving the formation of an aziridinium ion as an intermediate.
2004
10
1711
1714
A. DONDONI; B. RICHICHI; A. MARRA; D. PERRONE
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/340334
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