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Title: The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone
Authors: Guevara-Pulido, James Oswaldo
Andrés García, José María
Pedrosa Sáez, Rafael
Issue Date: 2015
Publisher: Royal Society of Chemistry
Description: Producción Científica
Citation: RSC Advances, 2015, 5, p. 65975-65981
Abstract: The reaction of enals with α,α′-diaryl-substituted acetones (pKa > 18) catalyzed by (S)-1-(2-pyrrolidinylmethyl) pyrrolidine provides direct access to enantioenriched 2,5,6-trisubstituted-3-hydroxy cyclohexanones. The process constitutes a highly stereoselective organocatalytic tandem Michael-intramolecular aldol reaction. It has been demonstrated that the stereoselection is dependent on the reaction conditions because only syn diastereoisomers are able to cyclize, and that anti diastereoisomers participate in a retro-Michael process decreasing the enantioselection.
Keywords: Química orgánica
ISSN: 2046-2069
Peer Review: SI
DOI: 10.1039/C5RA11215J
Sponsor: Ministerio de Economía, Industria y Competitividad (CTQ 2011-28487)
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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