Back to Search
Start Over
Enantioselective Synthesis of 2-Amino-1,1-diarylalkanes Bearing a Carbocyclic Ring Substituted Indole through Asymmetric Catalytic Reaction of Hydroxyindoles with Nitroalkenes
- Source :
- 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, RODERIC. Repositorio Institucional de la Universitat de Valéncia, instname, RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia
- Publication Year :
- 2018
- Publisher :
- American Chemical Society (ACS), 2018.
-
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.<br />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
- 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
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 83
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....fdb622fe2e5469a781e92e8a1fde83c7