773080-75-4Relevant academic research and scientific papers
Ring enlargement of polyhydroxylated pyrrolidines to piperidines by Mitsunobu reaction: A fortuitous synthesis of 1-deoxy-l-allonojirimycin
Dondoni, Alessandro,Richichi, Barbara,Marra, Alberto,Perrone, Daniela
, p. 1711 - 1714 (2004)
Chiral 3,4-dibenzyloxy-5-hydroxymethyl-2-thiazolylpyrrolidines under Mitsunobu conditions (R-OH, Ph3P, DIAD in THF, 80°C) 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. A piperidine derivative obtained in 74% yield was converted in four steps into the title allonojirimycin.
