Stereoselective synthesis of novel five-membered homoazasugars. A convenient route to all-cis tetrasubstituted pyrrolidines

Article abstract of DOI:10.1016/j.tetlet.2006.10.128

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 tan