Enantioselective total synthesis of (S)-(+)-lennoxamine through asymmetric hydrogenation mediated by l-proline-tetrazole ruthenium catalyst |
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Authors: | Yaneris Mirabal-GallardoJohanna Pié rola,Nagula ShankaraiahLeonardo S. Santos |
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Affiliation: | a Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, University of Talca, Talca, PO Box 747, Chile b Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad 500 037, India |
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Abstract: | A novel asymmetric synthetic strategy to prepare isoindolobenzazepine based lennoxamine alkaloid has been achieved in high ee% starting from 2-(benzo[d][1,3]dioxol-5-yl)ethanamine and 1-(chloromethyl)-2,3-dimethoxybenzene in 5 steps and with a 34% overall yield. The potentiality of this route involved the Bischler-Napieralsky cyclization that leads to tetracyclic indolinium skeleton, generation of chiral center through asymmetric hydrogen-transfer reaction employing l-proline-tetrazole as chiral ligand with Ru/Ir/Rh, and anodic oxidation as the key steps in the synthesis. |
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Keywords: | Isoindolobenzazepine Chilenamine Asymmetric hydrogenation reaction Anodic oxidation |
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