REDUCTIVE OPENING OF SATURATED OXA-CYCLE, AZA-CYCLE AND THIA-CYCLE BYMEANS OF AN ARENE-PROMOTED LITHIATION - SYNTHETIC APPLICATIONS

The treatment of different heterocycles With lithium in the presence o f an arene (naphthalene and 4,4'-di-tert-butylbiphenyl are the most fr equently used) in either a stoichiometric or catalytic amount gives fu nctionalized organolithium compounds, which by reacting with different electrophiles yield polyfunctionalized molecules. The reaction condit ions for the reductive opening of these systems depend on both the siz e and the nature of the heteroatom in the heterocycles.