Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/10061
Title: Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes
Authors: Nair, Divya K
Menna-Barreto, F. S
Silva Junior, Eufrânio N. da
Mobin, Shaikh M
Namboothiri, Irishi N. N
Affilliation: Indian Institute of Technology Bombay. Department of Chemistry. Mombai, India.
Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Rio de Janeiro, RJ, Brasil.
Universidade Federal de Minas Gerais. Departamento de Química. Instituto de Ciências Exatas. Belo Horizonte, MG, Brasil.
Indian Institute of Technology Bombay.National Single-Crystal X-Ray Diffraction Facility. Mumbai, India.
Indian Institute of Technology Bombay. Department of Chemistry. Mombai, India.
Abstract: Cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes using a quinine derived chiral squaramide organocatalyst led to the formation of pyranones and pyranonaphthoquinones in good to excellent yields and high diastereo- and enantioselectivities. Representative examples of the reaction scale-up with a much lower catalyst loading without an appreciable loss of selectivities and synthetic transformations of the products are also reported here. The compounds described herein for the first time were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease, since the structures are related to bioactive α-lapachones.
Keywords: Trypanosoma cruzi,
Chagas Disease
keywords: Trypanosoma cruzi,
Doença de Chagas
Issue Date: 2014
Publisher: Royal Society of Chemestry
Citation: NAIR, Divya K et al. Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes. Chem. Commun.,n.50, p. 6973-6976, 2014.
DOI: 10.1039/c4cc02279c
Copyright: open access
Appears in Collections:IOC - Artigos de Periódicos

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