Enantioselective Organophotocatalytic Telescoped Synthesis of a Chiral Privileged Active Pharmaceutical Ingredient |
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Authors: | Fabian Herbrik Dr Miguel Sanz Prof Alessandra Puglisi Dr Sergio Rossi Prof Maurizio Benaglia |
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Institution: | 1. Dipartimento di Chimica, Università degli Studi di Milano, Via Camillo Golgi 19, 20133 Milano, Italy;2. Taros Chemicals GmbH & Co. KG, Emil-Figge-Strasse 76 A, 44227 Dortmund, Germany |
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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 active pharmaceutical ingredient (API)synthesis was successfully achieved. The final process consists of four 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. |
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Keywords: | chiral API enantioselective catalysis flow chemistry organophotoredox catalysis telescoped process |
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