10.1021/ol303213r.s003
Alexandre Lumbroso
Alexandre
Lumbroso
Isabelle Beaudet
Isabelle
Beaudet
Loïc Toupet
Loïc
Toupet
Erwan Le Grognec
Erwan Le
Grognec
Jean-Paul Quintard
Jean-Paul
Quintard
Stereodivergent Synthesis of Iminosugars from Stannylated Derivatives of (<i>S</i>)‑Vinylglycinol
American Chemical Society
2013
Stereodivergent Synthesis
SS configuration
stereoselective epimerization
Stannylated Derivatives
enantiopure homonojirimycin analogs
metathesis reactions
dehydropiperidine
RS
stannylated oxazolidinones 5
tran
2013-01-04 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/Stereodivergent_Synthesis_of_Iminosugars_from_Stannylated_Derivatives_of_i_S_i_Vinylglycinol/2455567
An original access to iminosugars from a <i>cis</i>/<i>trans</i> mixture of stannylated oxazolidinones <b>5</b> is reported. The dehydropiperidines <b>7</b>-<i>trans</i> and <b>7</b>-<i>cis</i> were obtained stereoselectively with an <i>RS</i> and <i>SS</i> configuration depending on the order of the Sn–Li transmetalation (followed by electrophilic trapping) and of the ring closing metathesis reactions due to the stereoselective epimerization of the α-aminoanion intermediate. The dehydropiperidines <b>7</b>-<i>trans</i> and <b>7</b>-<i>cis</i> were subsequently used for the synthesis of enantiopure homonojirimycin analogs.