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Acyloins from Morita–Baylis–Hillman adducts: an alternative approach to the racemic total synthesis of bupropion

✍ Scribed by Giovanni W. Amarante; Patrícia Rezende; Mayra Cavallaro; Fernando Coelho

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
137 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

In this Letter, we describe an easy and straightforward strategy for the preparation of acyloins (a-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%.

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