Step economy strategy for the synthesis of amphoteric aminoaldehydes, key intermediates for reduced hydantoins

Despite of the orthogonal reactivity of the N–H aziridines aldehyde, these compounds exist as an equilibrium of three different forms – whereas the dimeric one is mostly observed in a variety of solvents. In this work, we have developed an alternative protocol for the aminoaldehyde dimers synthesis in two steps starting with an organocatalyzed aziridination between α,β-unsaturated aldehydes and a protected amine to afford known isolable and stable N-protected aziridine aldehydes. After Boc-deprotection, dimeric species were immediately formed from monomeric N–H aziridine aldehydes. From this building-block new reduced hydantoins were prepared via [3+2]-annulation with isocyanates.