[摘要]：Enantiopure 2,6-disubstituted morpholines were synthesized through the ring opening of chiral, nonracemic oxiranes with N nucleophiles, under solid-liq. phase-transfer catalysis (SL-PTC) conditions. The b-hydroxy tosylamide resulting from the ring opening of a first epoxide with 4-MeC6H4SO2NH2 was used as nucleophile, after protection of the OH group, in the reaction with a second oxirane. The morpholine skeleton was generated through std. functional group chem., followed by cyclization of the intermediate b-hydroxy b'-tosyloxy tosylamides carried out under SL-PTC conditions. The N-tosylmorpholines produced can be employed as building blocks in the synthesis of pharmaceuticals and as chiral tools.
