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Stereoselective synthesis of novel five-membered homoazasugars. A convenient route to all-cis tetrasubstituted pyrrolidines
Authors:Elena Moreno-Clavijo  Antonio J. Moreno-Vargas
Affiliation:Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, E-41071 Sevilla, Spain
Abstract:
We present a highly stereoselective procedure for the preparation of (2S and 2R,3S,4R,5S)-5-methyl-3,4-dihydroxy-2- ethoxycarbonylmethylpyrrolidines based on conjugate addition of ammonia to unsaturated aldonic esters derived from d-ribose followed by tandem cyclization. Derivatisation of these compounds to 2-hydroxyethyl-, benzymidazolylmethyl-, biphenyl-1-aminoethyl and naphthalene-l-aminoethyl-pyrrolidines is also presented.
Keywords:Pyrrolidines   Azasugars   Iminosugars   Imino-C-glycosides   Homoazasugars   Glycosidase inhibitors
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