Enantioselective aziridination of dienyl carbamates en route to sphingolipid mimics

Identifier:  TFM:2124

Handle: https://hdl.handle.net/20.500.11797/TFM2124

Authors:  Sánchez Quinteros, Marisa Katerin

Abstract:
The enantioselective aziridination of dienyl carbamates is crucial for synthesizing sphingolipid mimics. Previously, we devised a sequential oxyamination protocol that produced racemic oxazolidinones, which were transformed into enantioenriched sphingosine analogues. We then concentrated on metal-free intramolecular asymmetric oxyamination of alkenes via aziridination to improve enantioselective aziridine synthesis. Typically, hypervalent iodine reagents are eco-friendly oxidants for iminoiodanes or metallonitrenes generation. Our current study explores lactate-based (diacetoxyiodo)arenes as chiral reagents for the asymmetric oxyamination of dienyl carbamates, aiming to create innovative processes for synthesizing key intermediates and enhance the enantioselective synthesis of aziridines using I(III) reagents.