Polyfunctionalized benzo[d]sultams which contain an amino acid unit, have been synthesized from the corresponding open chain (pentafluorobenzene)sulfonamides by complementary solid-liquid phase transfer catalysis (SL-PTC) and homogeneous protocols. The cyclization step proceeds through the intramolecular nucleophilic displacement of an aromatic fluorine atom and leeds to the desired product with good ee's (50-88%) without any external source of chirality. The described procedure, toghether with the preferential crystallization of all the compounds allows the obtainment of optically pure benzosultams.
Synthesis of Enantiomerically Pure Polyfluorobenzo[d]sultams / A.l. Tagliabue ; D. Landini, M. Penso. DIPARTIMENTO DI CHIMICA ORGANICA E INDUSTRIALE, 2008 Dec 10. 21. ciclo, Anno Accademico 2007/2008. [10.13130/tagliabue-aaron-luca_phd2008-12-10].
Synthesis of Enantiomerically Pure Polyfluorobenzo[d]sultams
A.L. Tagliabue
2008
Abstract
Polyfunctionalized benzo[d]sultams which contain an amino acid unit, have been synthesized from the corresponding open chain (pentafluorobenzene)sulfonamides by complementary solid-liquid phase transfer catalysis (SL-PTC) and homogeneous protocols. The cyclization step proceeds through the intramolecular nucleophilic displacement of an aromatic fluorine atom and leeds to the desired product with good ee's (50-88%) without any external source of chirality. The described procedure, toghether with the preferential crystallization of all the compounds allows the obtainment of optically pure benzosultams.File | Dimensione | Formato | |
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