Atti del XXVI Congresso Nazionale della Società Chimica Italiana

The presence of a C-C double bond in polyfunctionalized organic molecules is a crucial requirement for the control of its biologically activity.(1) The importance of having a site in the molecule that is able to generate geometrical isomerization of a carbon-carbon double bond stimulated the development of new olefination methodologies. In particular, some efforts focused on the ability of Lewis acids to provide a cheap alternative for the synthesis of molecules with C-C double bond in a highly stereoselective fashion. For several years, we have been investigating CeCl3 promoted organic reactions. This Lewis acid has been found to efficiently promote carbon-carbon (2) and carbon-heteroatom bond formation reactions.(3) In addition to being green in nature (4), CeCl3 has been widely used for both inter- and intramolecular reactions for the synthesis of organic molecules with significant biological importance. Regarding the total synthesis of biologically active small molecules containing a carbon-carbon double bond, we saw the possibility to employ CeCl3 in the stereoselective construction of 2,3- dihydropyridones 1,(5) and 1,2-dihydroquinolines 2.(6)