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Manashi Panda
Oakland University
Enantioselective synthesisLewis acids and basesOrganic chemistryChemistryCycloaddition
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#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
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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).
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#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 4 authors...
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 product...
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