1. Enantioselective Synthesis of 2-Amino-1,1-diarylalkanes Bearing a Carbocyclic Ring Substituted Indole through Asymmetric Catalytic Reaction of Hydroxyindoles with Nitroalkenes
- Author
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Jaume Rostoll-Berenguer, Carlos Vila, José R. Pedro, Isabel Fernández, M. Carmen Muñoz, Rubén Sánchez-García, and Gonzalo Blay
- Subjects
Indole test ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Hydroxy group ,Enantioselective synthesis ,Alkylation ,010402 general chemistry ,Ring (chemistry) ,01 natural sciences ,Reaccions químiques ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,Catàlisi ,FISICA APLICADA ,Yield (chemistry) ,Química orgànica - Abstract
[EN] 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., Financial support from the MINECO (Gobierno de Espana; CTQ2017-84900-P) is gratefully acknowledged. C.V. thanks MINECO for a JdC contract. J.R.-B. thanks the Ministry of Education for a Collaboration grant. Access to NMR, MS, and X-ray facilities from the Servei Central de Suport a la Investigacio Experimental (SCSIE)-UV is also acknowledged
- Published
- 2018