Tandem nucleophilic addition/cyclization reaction in the synthesis of ketimine-type iminosugars.
The biological activity of unsaturated iminosugars has not yet been extensively studied because of a lack of general synthetic methods. A practical synthesis of these cyclic ketimine sugars was developed, which was based on a tandem addition-cyclization reaction of a Grignard reagent to a omega-methanesulfonylglycononitrile.
Behr
Jean-Bernard
JB
Institut de Chimie Moléculaire de Reims, UFR Sciences, CNRS, BP 1039, 51687 Reims Cedex 2, France. jb.behr@univ-reims.fr
Kalla
Adel
A
Harakat
Dominique
D
Plantier-Royon
Richard
R
D001554:Benzene / Q000737:chemistry; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry
D004952:Esters; D050111:Imino Sugars; D011758:Pyrroles; D001554:Benzene