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An approach to oxazolidin-2-ones from the Baylis–Hillman adducts. Formal synthesis of a chloramphenicol derivative

✍ Scribed by Fernando Coelho; Rodrigo C Rossi


Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
147 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis


In this communication we describe a straightforward and diastereoselective approach to prepare functionalised oxazolidin-2-ones from Baylis-Hillman adducts. A stereoselective synthesis of a highly substituted vicinal aminoalcohol and a formal synthesis of a chloramphenicol derivative are also described.


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Acyloins from Morita–Baylis–Hillman addu
✍ Giovanni W. Amarante; Patrícia Rezende; Mayra Cavallaro; Fernando Coelho 📂 Article 📅 2008 🏛 Elsevier Science 🌐 French ⚖ 137 KB

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 useful