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.