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.
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