Enantioselective total synthesis of (S)-(+)-lennoxamine through asymmetric hydrogenation mediated by L-proline-tetrazole ruthenium catalyst

dc.creatorMirabal-Gallardo, Y.
dc.creatorPierola, J.
dc.creatorShankaraiah, N.
dc.creatorSantos, L.S.
dc.date2012-12-17T19:11:17Z
dc.date2012-12-17T19:11:17Z
dc.date2012-07-11
dc.date.accessioned2017-03-07T14:59:06Z
dc.date.available2017-03-07T14:59:06Z
dc.identifierTETRAHEDRON LETTERS Volume: 53 Issue: 28 Pages: 3672-3675 DOI: 10.1016/j.tetlet.2012.05.033
dc.identifier0040-4039
dc.identifierhttp://dspace.utalca.cl/handle/1950/9155
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/376023
dc.descriptionSantos, LS (reprint author), Univ Talca, Chem Inst Nat Resources, Lab Asymmetr Synth, POB 747, Talca, Chile
dc.descriptionA 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. (C) 2012 Elsevier Ltd. All rights reserved.
dc.languageen
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
dc.subjectIsoindolobenzazepine
dc.subjectChilenamine
dc.subjectAsymmetric hydrogenation reaction
dc.subjectAnodic oxidation
dc.titleEnantioselective total synthesis of (S)-(+)-lennoxamine through asymmetric hydrogenation mediated by L-proline-tetrazole ruthenium catalyst
dc.typeArtículos de revistas


Este ítem pertenece a la siguiente institución