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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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Title Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita-Baylis-Hillman acetates of nitroalkenes
 
Creator NAIR, DK
MENNA-BARRETO, RFS
DA SILVA, EN
MOBIN, SM
NAMBOOTHIRI, INN
 
Subject ENANTIOSELECTIVE MICHAEL ADDITION
ALPHA-LAPACHONE
TRYPANOCIDAL ACTIVITY
TRYPANOSOMA-CRUZI
BETA-LAPACHONE
NAPHTHOQUINONES
DERIVATIVES
2-HYDROXY-1,4-NAPHTHOQUINONE
ORGANOCATALYSTS
CYCLOADDITION
 
Description 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 alpha-lapachones.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-12-28T11:35:57Z
2014-12-28T11:35:57Z
2014
 
Type Article
 
Identifier CHEMICAL COMMUNICATIONS, 50(53)6973-6976
1359-7345
1364-548X
http://dx.doi.org/10.1039/c4cc02279c
http://dspace.library.iitb.ac.in/jspui/handle/100/16374
 
Language English