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Type: Artigo de periódico
Title: Efficient synthesis of a new aminoazasugar and dihydroxyprolines from an endocyclic enecarbamate
Author: Pohlit, AM
Correia, CRD
Abstract: 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.
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Heterocycles. Pergamon-elsevier Science Ltd, v. 45, n. 12, n. 2321, n. 2325, 1997.
Rights: fechado
Date Issue: 1997
Appears in Collections:Unicamp - Artigos e Outros Documentos

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