An Alternative Approach to Aminodiols from Baylis-Hillman Adducts. Stereoselective Synthesis of Chloramphenicol, Fluoramphenicol and Thiamphenicol
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| Formato: | Artículo científico |
| Lenguaje: | en |
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Sociedad Química de México
2005
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| _version_ | 1876468200777973760 |
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| author | Cristiano R. Mateus |
| author_facet | Cristiano R. Mateus |
| contents | An Alternative Approach to Aminodiols from Baylis-Hillman Adducts. Stereoselective Synthesis of Chloramphenicol, Fluoramphenicol and Thiamphenicol Cristiano R. Mateus Fernando Coelho Multidisciplinaria (Ciencias Naturales y Exactas) α Baylis Hillman thiamphenicol chloramphenicol We describe herein a new approach for the stereoselective synthesis of broad spectrum antibioticsfrom Baylis-Hillman adducts. The strategy is based on the preparation of an ene-carbamate directlyfrom a Baylis-Hillman adduct using a Curtius rearrangement reaction. Stereoselective hydroborationfurnished a mixture of diastereoisomeric aminoalcohols (syn and anti). After chromatographicseparation, the syn diastereoisomer was directly transformed into the antibiotics. 2005 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47549212 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.2 Vol.49 |
| format | Artículo científico |
| id | redalyc_47549212 |
| institution | Redalyc |
| language | en |
| publishDate | 2005 |
| publisher | Sociedad Química de México |
| spellingShingle | An Alternative Approach to Aminodiols from Baylis-Hillman Adducts. Stereoselective Synthesis of Chloramphenicol, Fluoramphenicol and Thiamphenicol Cristiano R. Mateus Multidisciplinaria (Ciencias Naturales y Exactas) α Baylis Hillman thiamphenicol chloramphenicol An Alternative Approach to Aminodiols from Baylis-Hillman Adducts. Stereoselective Synthesis of Chloramphenicol, Fluoramphenicol and Thiamphenicol Cristiano R. Mateus Fernando Coelho Multidisciplinaria (Ciencias Naturales y Exactas) α Baylis Hillman thiamphenicol chloramphenicol We describe herein a new approach for the stereoselective synthesis of broad spectrum antibioticsfrom Baylis-Hillman adducts. The strategy is based on the preparation of an ene-carbamate directlyfrom a Baylis-Hillman adduct using a Curtius rearrangement reaction. Stereoselective hydroborationfurnished a mixture of diastereoisomeric aminoalcohols (syn and anti). After chromatographicseparation, the syn diastereoisomer was directly transformed into the antibiotics. 2005 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47549212 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.2 Vol.49 |
| title | An Alternative Approach to Aminodiols from Baylis-Hillman Adducts. Stereoselective Synthesis of Chloramphenicol, Fluoramphenicol and Thiamphenicol |
| topic | Multidisciplinaria (Ciencias Naturales y Exactas) α Baylis Hillman thiamphenicol chloramphenicol |
| url | https://www.redalyc.org/articulo.oa?id=47549212 |