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Title: Organocatalytic Domino Michael-Heterocyclization Reaction of Unsaturated Aldehydes and Cyano Ketones. Synthesis of Enantioenriched 4,5,6-Trisubstituted 3,4-Dihydropyranones
Authors: Guevara-Pulido, James Oswaldo
Andrés García, José María
Pedrosa Sáez, Rafael
Issue Date: 2014
Publisher: Wiley
Description: Producción Científica
Citation: European Journal of Organic Chemistry, 2014, Volume 2014, Issue 36, p. 8072–8076
Abstract: α,β-Unsaturated aldehydes with aliphatic, electron-poor aromatic, or electron-withdrawing substituents at the β position easily react with different ketones leading to enantioenriched hemiacetals, which were further oxidized to give 4,5,6-trisubstituted-3,4-dihydropyranones in good yields and with excellent enantioselectivities. The behavior of the ketones is dependent on the α substituent of the carbonyl group, and a fine-tuning of the pKa values is necessary to obtain good results.
Keywords: Química orgánica
ISSN: 1434-193X
Peer Review: SI
DOI: 10.1002/ejoc.201402982
Sponsor: Ministerio de Economía, Industria y Competitividad (CTQ2011-28487)
Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)
Universidad de Valladolid for a pre-doctoral fellowships
Publisher Version:
Language: eng
Rights: info:eu-repo/semantics/openAccess
Appears in Collections:CINQUIMA - Artículos de revista
DEP67 - Artículos de revista

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