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Type: Artigo de periódico
Title: Acyloins from Morita-Baylis-Hillman adducts: an alternative approach to the racemic total synthesis of bupropion
Author: Amarante, GW
Rezende, P
Cavallaro, M
Coelho, F
Abstract: In this Letter, we describe an easy and straightforward strategy for the preparation of acyloins (alpha-hydroxyketones) from Morita-Baylis-Hillman adducts.. based on a Curtius rearrangement. Different acyloins were obtained with good overall yield (>40% for three steps). To exemplify the synthetic usefulness of this strategy, total synthesis of (+/-)-bupropion, a dopamine, and nor-epinefrine reuptake inhibitor has been accomplished in eight steps with an overall yield of 25%. (C) 2008 Elsevier Ltd. All rights reserved.
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Rights: fechado
Identifier DOI: 10.1016/j.tetlet.2008.04.040
Date Issue: 2008
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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