CONCISE SYNTHESIS OF C2-SYMMETRIC TRANS-2,5-DIOXYMETHYLPYRROLIDINE DERIVATIVES BY NOVEL CYCLIZATION

Article abstract of DOI:10.1016/S0040-4039(01)80661-4

Treatment of (S)-1-benzyloxy-2-benzoylaminohex-5-ene with iodine in aqueous acetonitrile furnished (2S,5S)-5-benzoyloxymethyl-2-bemzyloxymethylpyrrolidine stereoselectively in a single step.The product was converted into C₂-symmetric (2S,5S)-2,5-dioxymethylpyrrolidines potentially utilizable as chiral auxiliaries and (2S,5S)-(-)-pyrrolidine-2,5-dicarboxylic acid isolated from marine alga Schizymenia dubyi.