Stereoselective Synthesis of Iminosugar‐ C ‐Glycosides through Addition of Organometallic Reagents to N ‐ tert ‐Butanesulfinyl Glycosylamines: A Comprehensive Study

A comprehensive study of the preparation and reactivity of N‐tert ‐butanesulfinyl glycosylamines with simple Grignard and organo lithium reagents in batch vs . continuous flow chemistry is reported. As they readily react as latent imine equivalents with a variety of carbon nucleophiles, these carbohydrate derivatives constitute very useful precursors for the diastereoselective synthesis of bioactive compounds such as iminosugar‐ C ‐glycosides. A hybrid protocol, involving the addition of benzylmagnesium chloride to a (S R )‐arabinofuranosylamine substrate in flow, at room temperature, combined with a cyclization protocol in batch is also described for the first time. Of note, this semi‐continuous flow process shortens the synthesis of imino‐ C ‐glycoside scaffolds to a single workday.