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Type: Artigo de periódico
Title: A highly enantioselective chemoenzymatic synthesis of syn-3-amino-2-hydroxy esters: key intermediates for taxol side chain and phenylnorstatine
Author: Rodrigues, JAR
Milagre, HMS
Milagre, CDF
Moran, PJS
Abstract: Starting from the bromination of alpha-ketoesters to obtain 3-bromo-2-oxoalkanoates and bioreduction with Saccharomyces cerevisiae entrapped in calcium alginate pellets with double gel layers, syn-(2R,3S)-beta-bromo-alpha-hydroxy esters were obtained regioselectively in high yields and high ee. These chiral bromohydrins were cyclized to epoxides that were transformed into oxazolidines and finally opened by acidic hydrolysis to give syn-(2S,3S)-beta-amino-alpha-hydroxy esters in high overall yields and high ee. The enantiomeric excesses of all the intermediates were maintained during the reaction sequence. (C) 2005 Elsevier Ltd. All rights reserved.
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron-asymmetry. Pergamon-elsevier Science Ltd, v. 16, n. 18, n. 3099, n. 3106, 2005.
Rights: fechado
Identifier DOI: 10.1016/j.tetasy.2005.08.015
Date Issue: 2005
Appears in Collections:Unicamp - Artigos e Outros Documentos

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