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Issue 53, 2014
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Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes

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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.

Graphical abstract: Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes

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Publication details

The article was received on 27 Mar 2014, accepted on 29 Apr 2014 and first published on 29 Apr 2014


Article type: Communication
DOI: 10.1039/C4CC02279C
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Chem. Commun., 2014,50, 6973-6976

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    Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes

    D. K. Nair, R. F. S. Menna-Barreto, E. N. da Silva Júnior, S. M. Mobin and I. N. N. Namboothiri, Chem. Commun., 2014, 50, 6973
    DOI: 10.1039/C4CC02279C

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