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Keywords = Phenyliodonium ylides

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15 pages, 2549 KiB  
Article
Chiral Dirhodium(II) Carboxylates: New Insights into the Effect of Ligand Stereo-Purity on Catalyst Structure and Enantioselectivity
by Frady G. Adly, Hannah Bollard, Michael G. Gardiner and Ashraf Ghanem
Catalysts 2018, 8(7), 268; https://doi.org/10.3390/catal8070268 - 30 Jun 2018
Cited by 6 | Viewed by 5539
Abstract
The current report contributes to the understanding of the stereoselectivity of chiral dirhodium(II) carboxylate catalysts carrying N-protected tert-leucine ligands. Investigating the possible effect of ligand stereo-purity on catalyst structure and enantioselectivity was carried out. This was justified through a new X-ray [...] Read more.
The current report contributes to the understanding of the stereoselectivity of chiral dirhodium(II) carboxylate catalysts carrying N-protected tert-leucine ligands. Investigating the possible effect of ligand stereo-purity on catalyst structure and enantioselectivity was carried out. This was justified through a new X-ray crystal structure for Rh2(S,S,S,R-PTTL)4 diastereomer. Full article
(This article belongs to the Special Issue Asymmetric Catalysis in Organic Synthesis)
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12 pages, 236 KiB  
Article
A Survey on the Reactivity of Phenyliodonium Ylide of 2-Hydroxy-1,4-Naphthoquinone with Amino Compounds
by Konstantina Spagou, Elizabeth Malamidou-Xenikaki and Spyros Spyroudis
Molecules 2005, 10(1), 226-237; https://doi.org/10.3390/10010226 - 31 Jan 2005
Cited by 14 | Viewed by 8928
Abstract
The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo [...] Read more.
The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo compounds. Arylhydrazines are mainly oxidized by the ylide and arylation occurs only in a low yield. Full article
(This article belongs to the Special Issue Hypervalent Iodine)
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9 pages, 48 KiB  
Article
Enantioselective Intramolecular CH-Insertions upon Cu-Catalyzed Decomposition of Phenyliodonium Ylides
by Paul Müller and Christelle Boléa
Molecules 2001, 6(3), 258-266; https://doi.org/10.3390/60300258 - 28 Feb 2001
Cited by 33 | Viewed by 8321
Abstract
The Cu-catalyzed intramolecular CH insertion of phenyliodonium ylide 5b has been investigated at 0° C in the presence of several chiral ligands. Enantioselectivities vary in the range of 38–72 %, and are higher than those resulting from reaction of the diazo compound 5c [...] Read more.
The Cu-catalyzed intramolecular CH insertion of phenyliodonium ylide 5b has been investigated at 0° C in the presence of several chiral ligands. Enantioselectivities vary in the range of 38–72 %, and are higher than those resulting from reaction of the diazo compound 5c at 65° C. The results are consistent with a carbenoid mechanism for Cu-catalyzed decomposition of phenyliodonium ylides. Full article
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