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

Published on Aug 28, 2019in Journal of Organic Chemistry4.335
· DOI :10.1021/ACS.JOC.9B01854
Mukulesh Mondal10
Estimated H-index: 10
(Oakland University),
Manashi Panda8
Estimated H-index: 8
(Oakland University)
+ 1 AuthorsNessan J. Kerrigan14
Estimated H-index: 14
(DCU: Dublin City University)
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Abstract
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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#1Denis D. Borisov (RAS: Russian Academy of Sciences)H-Index: 5
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Ring-opening transformations of donor-acceptor cyclopropanes (DAC) with carbon-centered nucleophiles is a simple, straight-forward approach to 1,3-bifunctional compounds that has witnessed a remarkable progress over the past several years. To date, different reactivity patterns of DACs’ has been successfully exploited in racemic/ stereoselective syntheses of various acyclic compounds or carbocycles with an impressive structural diversity. The thriving strategies has been successfully utilized in...
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#1Alexander Lücht (Braunschweig University of Technology)H-Index: 6
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