Switchable Reactivity of Cyclopropane Diesters toward (3 + 3) and (3 + 2) Cycloadditions with Benzoquinone Esters
Navpreet Kaur, Pankaj Kumar, Arijit Hazra, Prabal Banerjee
Abstract
Herein, we describe an unprecedented (3 + 3) cycloaddition reaction of the donor-acceptor cyclopropanes with quinone esters toward the construction of chroman scaffolds in moderate to good yields. Interestingly, the strategy is also adjustable toward a (3 + 2) cycloaddition by just switching the Lewis acid to furnish benzofuran scaffolds. Based on the choice of Lewis acid used, the same set of precursors has been used to deliver the benzopyran and benzofuran derivatives.
Topics & Concepts
ChemistryCycloadditionCyclopropaneLewis acids and basesBenzofuranReactivity (psychology)BenzoquinoneQuinoneCombinatorial chemistryOrganic chemistryStereochemistryRing (chemistry)CatalysisMedicinePathologyAlternative medicineCyclopropane Reaction MechanismsCatalytic Alkyne ReactionsAsymmetric Synthesis and Catalysis