Organocatalytic oxa-Michael/Michael Addition/Deformylation Cascade Reaction of 3-Formylchromone with p-Quinol: Synthesis of the Furanochromanone Skeleton

An approach for the construction of furanochromanone skeletons has been developed through a DABCO-catalyzed cascade reaction with good yields (up to 83%) and high diastereoselectivity (> 20:1 dr). Notably, the asymmetric catalytic version of this reaction was further studied, obtaining furanochromanones bearing four contiguous stereogenic centers with excellent enantio- and diastereoselectivity (up to 98% ee, > 20:1 dr). This protocol causes the formation of a variety of substituted furanochromanones via an oxaMichael/Michael addition/deformylation cascade reaction.

Automated summary

A DABCO-catalyzed cascade reaction was used to construct furanochromanone skeletons with high yields and diastereoselectivity. The asymmetric catalytic version of this reaction also showed excellent enantio- and diastereoselectivity, producing furanochromanones with multiple stereogenic centers.