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Stereodivergent Synthesis of Iminosugars from Stannylated Derivatives of (S)‑Vinylglycinol

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posted on 04.01.2013, 00:00 authored by Alexandre Lumbroso, Isabelle Beaudet, Loïc Toupet, Erwan Le Grognec, Jean-Paul Quintard
An original access to iminosugars from a cis/trans mixture of stannylated oxazolidinones 5 is reported. The dehydropiperidines 7-trans and 7-cis were obtained stereoselectively with an RS and SS 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 7-trans and 7-cis were subsequently used for the synthesis of enantiopure homonojirimycin analogs.