Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes
2019
Mondal, Mukulesh | Panda, Manashi | McKee, Vickie | Kerrigan, Nessan J.
In this article we describe a new asymmetric synthesis of highly substituted tetrahydrofurans through a Pd(PPh₃)₄-catalyzed formal [3 + 2]-cycloaddition of donor–acceptor cyclopropanes and ketenes. The desired structural motif was formed in moderate to excellent yields (42–84% for 16 examples), with excellent Z:E isomer diastereoselectivity (≥19:1 for 16 examples), and with good to excellent enantioselectivity in all cases examined (83–97% ee for 6 examples). The synthetic utility of the products was illustrated by a number of diastereoselective transformations into reduced tetrahydrofurans and spirocyclic tetrahydrofuran-barbiturate derivatives.
Afficher plus [+] Moins [-]Mots clés AGROVOC
Informations bibliographiques
Cette notice bibliographique a été fournie par National Agricultural Library
Découvrez la collection de ce fournisseur de données dans AGRIS
