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oai:riubu.ubu.es:10259/42882021-11-10T09:38:24Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Synthesis of α-functionalized α-indol-3-yl carbonyls through direct SN reactions of indol-3-yl α-acyloins Suárez, Anisley Martínez Lara, Fernando Sanz Díez, Roberto Química orgánica Chemistry, Organic A new and efficient synthesis of α-functionalized α-indol-3-yl ketones from easily available indolyl α-acyloins is reported. This process, catalyzed by Brønsted or Lewis acids, involves an uncommon direct nucleophilic substitution reaction of a secondary α-carbonyl-substituted hydroxyl group. The described methodology allows the introduction of a variety of nucleophiles such as (hetero)arenes, thiophenols, nitroanilines and 1,3-dicarbonyl derivatives. The synthesized α-indol-3-yl carbonyl compounds are important synthetic targets also useful for accessing functionalized tryptophols and furan-3-yl indoles. Ministerio de Economía y Competitividad (MINECO) (CTQ2013-48937-C2-1-P) and Junta de Castilla y León and FEDER (BU237U13 and BU076U16) 2016-12-01T10:00:54Z 2017-12-21T03:45:06Z 2016-12 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 1477-0520 http://hdl.handle.net/10259/4288 10.1039/c6ob02125e eng Organic & Biomolecular Chemistry. 2016, V. 14, n. 47, p. 11212-11219 http://dx.doi.org/10.1039/c6ob02125e info:eu-repo/grantAgreement/MINECO/CTQ2013-48937-C2-1-P info:eu-repo/grantAgreement/JCyL-FEDER/BU237U13 info:eu-repo/grantAgreement/JCyL-FEDER/BU076U16 info:eu-repo/semantics/openAccess application/pdf Royal Society of Chemistry https://riubu.ubu.es/bitstream/10259/4288/4/Su%c3%a1rez-OBC_2016%2c.pdf.jpg Hispana TEXT http://rightsstatements.org/vocab/CNE/1.0/ RIUBU. Repositorio Institucional de la Universidad de Burgos http://hdl.handle.net/10259/4288