A Modular Approach to the Synthesis of Morpholines

Significance

Building upon previous work on the ring opening of enantiopure aziridines and azetidines, the authors report a straightforward and practical approach to the synthesis of morpholines (J. Org. Chem. 2007, 72, 5859). The strategy involves a stereospecific one-pot intermolecular ring opening of readily available, enantiomerically enriched aziridines and azetidines with haloalcohols, followed by intramolecular cyclization in the presence of a base to provide morpholine derivatives. The importance of morpholines in medicinal chemistry and the modularity of this approach give value to this strategy.