Artículos de revistas
Acyloins from Morita-Baylis-Hillman adducts: an alternative approach to the racemic total synthesis of bupropion
Registro en:
Tetrahedron Letters. Pergamon-elsevier Science Ltd, v. 49, n. 23, n. 3744, n. 3748, 2008.
0040-4039
WOS:000256378800009
10.1016/j.tetlet.2008.04.040
Autor
Amarante, GW
Rezende, P
Cavallaro, M
Coelho, F
Institución
Resumen
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. 49 23 3744 3748