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.

Mechanistic investigation of aziridine aldehyde-driven peptide macrocyclization: the imidoanhydride pathway

Aziridine aldehydes participate in a multicomponent reaction with α-amino amides and isocyanides to generate reactive imidoanhydride intermediates.

Bicycle synthesis through peptide macrocyclization using aziridine aldehydes followed by late stage disulfide bond installation

We present a method that can be applied to generate medium-sized peptidomimetic macrocycles equipped with disulfide bonds.