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One-pot synthesis of unsymmetrical squaramides and their application in organocatalytic henry reactions

AuthorsAlegre-Requena, Juan V. ; Marqués-López, Eugenia ; Herrera, Raquel P.
Issue Date2015
CitationXII Simposio de Investigadores Jóvenes RSEQ Sigma-Aldrich (2015)
AbstractIn this work, we developed the first one-‐pot synthesis of unsymmetrical squaramides. Following this methodology, we prepared the most common bifunctional squaramide-­ based organocatalysts, obtaining in most cases better yields compared to those obtained in the analogous step-­by-­step syntheses. Also, we developed additional syntheses of squaramides that have been used in other areas besides catalysis, such as biologically active squaramides in medicinal chemistry. This new synthetic approach could make the use of squaramides more appealing for different industrial processes. Furthermore, using this one‐pot approach, we synthesized new chiral squaramides that were employed in the asymmetric Henry reaction. Diverse enantiomerically enriched nitroaldol products were obtained in good yields and enantioselectivities (up to 94% ee) under mild conditions and using a low catalyst loading of 0.25–2.5 mol%. This represents the lowest catalyst loading that has been used for this type of reaction in the organocatalytic field up to date.
DescriptionResumen del póster presentado al XII Simposio de Investigadores Jóvenes de la Real Sociedad Española de Química Sigma-Aldrich, celebrado en Barcelona del 3 al 6 de noviembre de 2015.
Appears in Collections:(ISQCH) Comunicaciones congresos
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