Enantioselective organophotocatalytic telescoped synthesis of a chiral privileged active pharmaceutical ingredient
Articolo
Data di Pubblicazione:
2022
Citazione:
Enantioselective organophotocatalytic telescoped synthesis of a chiral privileged active pharmaceutical ingredient / F. Herbrik, M. Sanz, A. Puglisi, S. Rossi, M. Benaglia. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 28:33(2022 Jun 10), pp. e202200164.1-e202200164.7. [10.1002/chem.202200164]
Abstract:
The continuous flow, enantioselective, organophotoredox catalytic asymmetric alkylation of aldehydes was studied, by using a homemade, custom designed photoreactor for reactions under cryogenic conditions. Going from microfluidic conditions up to a 10 mL mesofluidic reactor, an increase of productivity by almost 18000% compared to the batch reaction was demonstrated. Finally, for the first time, a stereoselective photoredox organocatalytic continuous flow reaction in a fully telescoped process for an API synthesis was successfully achieved. The final process consists of 4 units of operation: visible light-driven asymmetric catalytic benzylation under continuous flow, inline continuous work-up, neutralisation and a final oxidative amidation step afforded the pharmaceutically active molecule in 95% e.e.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
chiral API; enantioselective catalysis; flow chemistry; organophotoredox catalysis; telescoped process;
Elenco autori:
F. Herbrik, M. Sanz, A. Puglisi, S. Rossi, M. Benaglia
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