An Alternative Approach to Aminodiols from Baylis-Hillman Adducts. Stereoselective Synthesis of Chloramphenicol, Fluoramphenicol and Thiamphenicol


  • Cristiano R. Mateus Universidade Estadual de Campinas
  • Fernando Coelho Universidade Estadual de Campinas


Chloramphenicol, Baylis-Hillman, fluoramphenicol, thiamphenicol, α-hydroxymethylketones


Abstract. We describe herein a new approach for the stereoselective synthesis of broad spectrum antibiotics from Baylis-Hillman adducts. The strategy is based on the preparation of an ene-carbamate directly from a Baylis-Hillman adduct using a Curtius rearrangement reaction. Stereoselective hydroboration furnished a mixture of diastereoisomeric aminoalcohols (syn and anti). After chromatographic separation, the syn diastereoisomer was directly transformed into the antibiotics.



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Author Biographies

Cristiano R. Mateus, Universidade Estadual de Campinas

Instituto de Química

Fernando Coelho, Universidade Estadual de Campinas

Instituto de Química


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