Construction of Enantioenriched 4,5,6,7‐Tetrahydrofuro[2,3‐<i>b</i>]pyridines through a Multicatalytic Sequence Merging Gold and Amine Catalysis
Manon Genet, Abdelilah Takfaoui, Jérôme Marrot, Christine Greck, Xavier Moreau
Abstract
Abstract A series of enantioenriched 4,5,6,7‐tetrahydrofuro[2,3‐ b ]pyridines were accessed by a cycloisomerization/cycloaddition strategy. Starting from ynamide derivatives and aldehydes, yields ranging from 27 to 90% and high levels of stereoselectivity (de>95%, 93–99% ee) were obtained through sequential relay catalysis. The concurrent use of a gold complex with a diphenylprolinol silyl ether was applied to a combination of diversely functionalized substrates. magnified image
Topics & Concepts
ChemistryCycloisomerizationCatalysisCycloadditionStereoselectivityCombinatorial chemistryAmine gas treatingSequence (biology)SilylationStereochemistryOrganic chemistryBiochemistryCatalytic Alkyne ReactionsChemical synthesis and alkaloidsTraditional and Medicinal Uses of Annonaceae