This PhD work has been focused in two different subjects : - The stereoselective synthesis of 2,2-disubstituted chroman moiety assisted by sulfoxides as only source of chirality has been realized with good yields and good diastereoselectivities. The total synthesis of the natural metabolite of tocopherol, (S)-γ-CEHC, has been realized in ten steps and in 18.4% of overall yield using as key step the formation of ally sulfinyl chroman by reaction with allyl trimethyl silane in the presence of a Lewis acid. - The stereoselective synthesis of monofluorinated trisusbtituted olefins has been realized in moderated yields and excellents selectivities in some cases (95 :5) from readily available 3,3,3-trifluoropropionates.The Diels-Alder reaction using fluorinated dienophiles and cyclopentadiene led to unexpected complex structures.
| Identifer | oai:union.ndltd.org:CCSD/oai:tel.archives-ouvertes.fr:tel-01064056 |
| Date | 16 January 2012 |
| Creators | Lecea Romera, Mercedes |
| Publisher | Université de Strasbourg |
| Source Sets | CCSD theses-EN-ligne, France |
| Language | English |
| Detected Language | English |
| Type | PhD thesis |
Page generated in 0.0025 seconds