3,4]oxadiazinan-2-one (6) is an easily available building block and acts as a chiral non-racemic precursor for azomethine imines. The ylid can be formed regioselectively with various aldehydes and reacts in an efficient manner with a wide range of dipolarophiles. The regio-and diastereoselectivity of the cycloadditions have been fully investigated and can lead, in the best cases, to the creation of three contiguous asymmetric centers in a single step, with complete control of relative and absolute configurations.

The use of structurally similar chiral non-racemic azomethine ylides, nitrones and azomethine imines derived from 1,2-aminol alcohols in asymmetric dipolar cycloadditions is reviewed. This general survey underlines the great synthetic potential of dipolar cycloadditions, especially in a diversity-oriented approach and enables a direct comparison of the reactivity of apparently closely related reactive systems.