Synthesis and applications of chiral N-sulfinylimines and -aziridines as versatile building blocks in organic chemistry

Abstract

Nucleophilic ring opening of N-protected aziridines is known as one of the scarce methods for the incorporation of a protected amino-ethyl unit (-CR1R2CR3R4NR5R6) in a stereo- and regioselective way in organic synthesis. This amino-ethyl unit can be found in a wide range of natural products and N-containing drugs. These N-protected aziridines constitute an important group of target molecules in the synthetic organic chemistry, due to their biological activity as well as their structural complexity. This PhDthesis comprises the development of new chiral N-sulfinylaziridines, using a diastereoselective Mannich-type addition of N-protected glycine derivatives across chiral α-functionalized-N sulfinylimines. Hereby, an efficient synthesis of a wide range of new chiral aziridines is presented which can be applied as starting products for the synthesis of new heterocyclic compounds