Synthesis of 2,6-disubstituted morpholines through regioselective oxiranes ring opening by tosylamide under PTC conditions

Symmetric and non-symmetric 2,6-disubstituted morpholines were synthesized through regioselective nucleophilic ring opening of oxiranes with tosylamide under solid-liquid phase transfer catalysis (SL-PTC) conditions followed by cyclization of the tosylamido diols thus obtained and final deprotection of the corresponding N-tosyl morpholines. The morpholines prepared are interesting building blocks in the synthesis of pharmaceuticals and agrochemicals. --------------------------------------------------------------------------------