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Organocatalytic hydrophosphonylation promoted by hydrogen bond based catalyst

AuthorsAlegre-Requena, Juan V. ; Marqués-López, Eugenia ; Herrera, Raquel P.
Issue Date2013
Citation5th ORCA Meeting and Training School (2013)
AbstractThe addition of dialkylphosphites and diarqlphosphites to carbonyi compounds (Pudovik reaction) is a powerful and widely applied strategy for constructing C-P bonds, and a straightforward tool for providing efficient access to chiral a-hydroxy phosphonates and their corresponding phosphonic acids. Interestingly, compounds bearing this motif have shown remarkable biological activities and are commonly employed in the pharmaceutical industry. Although the Pudovik reaction of aldehydes has been the focus of intensive studies using chiral metal catalysts giving access to a-hydroxy phosphonates with good outcomes, the organocatalytic version of this appealing strategy has been overlooked in the literature. We want to report here our results concerning the first squaramide-catalyzed hydrophosphonylation of aldehydes. In all cases, the reaaions proceeded smoothly and cleanly under very mild conditions rendering final α-hydroxy phosphonates in verq good yields and high enantioselectivitiec. It is the first time that diphenylphosphite has been successfully employed in this reaction in contrast to the dialkylphosphites used in previously published procedures, extending the generality of this asymmetric methodology.
DescriptionTrabajo presentado al 5th OrganoCatalysis Cost Action (ORCA) Meeting and Training School celebrado en Alicante (España) del 17 al 19 de octubre de 2013.
Publisher version (URL)https://sites.google.com/site/5thorcameetingalicante/
Appears in Collections:(ISQCH) Comunicaciones congresos
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