Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 18, Pages 11983-11991Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01854
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Funding
- National Science Foundation [CHE-1463728]
- Carlsberg Foundation [CF15-0675]
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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 (83-7% 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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