Stereoselective Synthesis of Epoxyhydroxylamines and 1,2-Oxazetidines

Significance

The report describes a rapid method to prepare enantiopure epoxyhydroxylamines 3 and 1,2-oxazetidines 4 from chiral epoxides. The success of the method is important in that the corresponding reaction was reported not to work with carbonyl moieties (by the same authors). The densely functionalized hydroxylamines 3 undergo a regioselective epoxide opening in basic conditions to form the sterically congested 4. None of the 5-endo product 5 was observed. Noteworthy is that the oxazetidines 4 are stable and can be isolated by chromatography.