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.
10-dic-2008
sultam ; polyfluorobenzosultam ; self-induction of chirality ;
Settore CHIM/04 - Chimica Industriale
LANDINI, DARIO
FERRUTI, PAOLO
Doctoral Thesis
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].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/63056
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