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One-pot sequential organocatalytic Michael-Tishchenko-lactonization reactions. Synthesis of enantioenriched 4,5,6-trisubstituted δ-lactones

Authors :
James O. Guevara-Pulido
José M. Andrés
Rafael Pedrosa
Source :
UVaDOC. Repositorio Documental de la Universidad de Valladolid, instname
Publication Year :
2014

Abstract

Producción Científica<br />Enantioenriched trisubstituted lactones were obtained in good yields and moderate to very good enantioselectivities in one-pot process, which implies a sequential organocatalyzed Michael addition of ketones to enals, followed by catalytic intramolecular diastereoselective Tishchenko reaction and lactonization. The final lactones were obtained as single diastereoisomers, demonstrating that the mixture of the anti and syn diastereomers epimerized to the syn hydroxy ester during the oxido-reduction step.<br />Ministerio de Economía, Industria y Competitividad (CTQ 2011-28487)<br />Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)<br />Universidad de Valladolid for a pre-doctoral fellowships

Details

ISSN :
15206904
Volume :
79
Issue :
18
Database :
OpenAIRE
Journal :
The Journal of organic chemistry
Accession number :
edsair.doi.dedup.....5ef3c3364f5772b081b8c9ce72dd1f28