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

Published on Sep 20, 2019in Journal of Organic Chemistry4.745
· DOI :10.1021/acs.joc.9b01854
Mukulesh Mondal1
Estimated H-index: 1
(Oakland University),
Manashi Panda1
Estimated H-index: 1
(Oakland University)
+ 1 AuthorsNessan J. Kerrigan1
Estimated H-index: 1
(DCU: Dublin City University)
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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Cited By1
#1Alexander Lücht (Braunschweig University of Technology)H-Index: 4
#2Alexander Kreft (Braunschweig University of Technology)H-Index: 4
Last. Daniel B. Werz (Braunschweig University of Technology)H-Index: 35
view all 4 authors...
#1Mukulesh Mondal (Oakland University)H-Index: 1
#2Manashi Panda (Oakland University)H-Index: 1
Last. Nessan J. Kerrigan (DCU: Dublin City University)H-Index: 1
view all 5 authors...
When InBr3-EtAlCl2 (15–30 mol%) was used as a dual Lewis acid system to promote the formal [3+2]-cycloaddition of enantioenriched donor–acceptor cyclopropanes with ketenes, cyclopentanones were formed in good to excellent yields (84–99%, 18 examples), and with excellent transfer of chirality (15 examples, 90% ee to >99% ee).