Enantioselective synthesis of 2‑amino-1,1-diarylalkanes bearing a carbocyclic ring substituted indole through asymmetric catalytic reaction of hydroxyindoles with nitroalkenes
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Enantioselective synthesis of 2‑amino-1,1-diarylalkanes bearing a carbocyclic ring substituted indole through asymmetric catalytic reaction of hydroxyindoles with nitroalkenes

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Enantioselective synthesis of 2‑amino-1,1-diarylalkanes bearing a carbocyclic ring substituted indole through asymmetric catalytic reaction of hydroxyindoles with nitroalkenes

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Vila Descals, Carlos; Rostoll-Berenguer, Jaume; Sánchez-García, Rubén; Blay Llinares, Gonzalo Perfil; Fernández Picot, Isabel; Muñoz, M. Carmen; Pedro, José Ramón
This document is a artículoDate2018
An asymmetric catalytic reaction of hydroxyindoles with nitroalkenes leading to the Friedel−Crafts alkylation in the carbocyclic ring of indole is presented. The method is based on the activating/directing effects of the hydroxy group situated in the carbocyclic ring of the indole providing nitroalkylated indoles functionalizated at the C-4, C-5, and C-7 positions with high yield, regio-, and enantioselectivity. The optically enriched nitroalkanes were transformed efficiently in optically enriched 2-amino-1,1-diarylalkanes bearing a carbocyclic ring substituted indole.

    Vila Descals, Carlos Rostoll-Berenguer, Jaume Sánchez-García, Rubén Blay Llinares, Gonzalo Fernández Picot, Isabel Muñoz, M. Carmen Pedro, José Ramón 2018 Enantioselective synthesis of 2‑amino-1,1-diarylalkanes bearing a carbocyclic ring substituted indole through asymmetric catalytic reaction of hydroxyindoles with nitroalkenes Journal of Organic Chemistry 83 6397 6407
https://doi.org/10.1021/acs.joc.8b00612

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