Palladium‐Catalyzed [4+2] Cycloaddition of Hydroxy‐Tethered Allylic Carbonates with Alkenes: Synthesis of Functionalized Tetrahydropyrans
Jiaqing Xu, Wangyu Shi, Min Liu, Jianning Liao, Wei Wang, Yongjun Wu, Hongchao Guo
Abstract
Abstract A palladium‐catalyzed [4+2] cycloaddition of hydroxy‐tethered allyl carbonates with five types of electron‐deficient alkenes has been achieved, in which a type of new hydroxy‐tethered allyl carbonates acted as valuable precursors for the formation of 1,4‐C,O‐dipole allylpalladium intermediates. The reaction proceeded efficiently under mild reaction conditions to provide the corresponding tetrahydropyran derivatives in moderate to high yields with excellent diastereoselectivities. magnified image
Topics & Concepts
ChemistryCycloadditionPalladiumAllylic rearrangementCatalysisTetrahydropyranMedicinal chemistryOrganic chemistryRing (chemistry)Catalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods