title: Stereodivergent synthesis of iminosugars from stannylated derivatives of (S)-vinylglycinol.
abstract: 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.
authors.affiliation: Université de Nantes CNRS, CEISAM, UMR 6230, Faculté des Sciences et des Techniques, 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3 France.
authors.forename: Alexandre
authors.initials: A
authors.lastname: Lumbroso
authors.forename: Isabelle
authors.initials: I
authors.lastname: Beaudet
authors.forename: Loïc
authors.initials: L
authors.lastname: Toupet
authors.forename: Erwan
authors.initials: E
authors.lastname: Le Grognec
authors.forename: Jean-Paul
authors.initials: JP
authors.lastname: Quintard
mesh_terms: D044948:Flavonols / Q000737:chemistry*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009947:Organotin Compounds / Q000737:chemistry*; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D044948:Flavonols; D050111:Imino Sugars; D009947:Organotin Compounds; D023303:Oxazolidinones; D014753:Vinyl Compounds; C540862:glycinol