Asymmetric Synthesis of Tetrahydrofurans through Palladium(0)-Catalyzed [3 + 2]-Cycloaddition of Vinylcyclopropanes with Ketenes

Mukulesh Mondal, Manashi Panda, Vickie McKee, Nessan J. Kerrigan*

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Abstrakt

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. ©

OriginalsprogEngelsk
TidsskriftJournal of Organic Chemistry
Vol/bind84
Udgave nummer18
Sider (fra-til)11983-11991
Antal sider9
ISSN0022-3263
DOI
StatusUdgivet - 20. sep. 2019

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