Organocatalytic oxa‐Michael/Michael Addition/Deformylation Cascade Reaction of 3‐Formylchromone with <i>p</i>‐Quinol: Synthesis of the Furanochromanone Skeleton
Xiurong Zheng, Jiajia Chen, Zhuowen Li, Lin Zhong, Ruoting Zhan, Huicai Huang
Abstract
Abstract 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 oxa‐Michael/Michael addition/deformylation cascade reaction. magnified image
Topics & Concepts
Michael reactionStereocenterChemistryDABCOCascadeCascade reactionCatalysisOrganocatalysisStereochemistryEnantioselective synthesisOrganic chemistryChromatographySynthesis of Organic CompoundsOxidative Organic Chemistry ReactionsCarbohydrate Chemistry and Synthesis