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Communication | Regular issue | Vol 45, No. 12, 1997, pp.2321-2325
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7974
Efficient Synthesis of a New Aminoazasugar and Dihydroxyprolines from an Endocyclic Enecarbamate

Adrian M. Pohlit and Carlos Roque D. Correia*

*Instituto de Química, Universidade Estadual de Campinas (UNICAMP), Caixa Postal 6154, CEP 13083-970, Campinas, Sao Paulo, Brazil


A novel procedure for the synthesis of trans-2,3-(2-aminomethyl)-cis-3,4-dihydroxypyrrolidine (a new aminoazasugar) and cis-2,3- and trans-2,3-cis-3,4-dihydroxyprolines is presented. Starting from the known endocyclic enecarbamate 1-carbobenzyloxy-2-pyrroline, the above compounds were efficiently synthesized in 6 or 7 steps in good overall yields. In the key step, trans-2,3-(1-carbobenzyloxy)-cis-3,4-diacetyloxy-2-methoxypyrrolidine underwent Lewis acid promoted cyanation, presumably via the corresponding N-acyliminium ion.