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Enantio- and regioselective CpRu-catalyzed Carroll rearrangement.
- Source :
-
Pure & Applied Chemistry . May2008, Vol. 80 Issue 5, p967-977. 11p. - Publication Year :
- 2008
-
Abstract
- Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194The addition of unstabilized carbonyl nucleophiles to allyl-metal fragments still represents a challenge for generating stereoselectively tertiary (and quaternary) stereogenic centers. In this context, the decarboxylative Carroll rearrangement of secondary and tertiary allyl β-ketoesters is particularly interesting since chiral γ,δ-unsaturated ketones are obtained. Herein, we show that CpRu half-sandwich complexes can, in the presence of selected enantiopure diimine ligands, catalyze this transformation and afford complete conversions and decent level of enantiomeric excess. Zwitterionic adducts of a hexacoordinated phosphorus anion and CpRu moieties were also associated and shown to generate air-, moisture-, and microwave-stable catalysts that can be readily purified and recycled. Carroll rearrangements of allylic β-ketoesters performed with these zwitterionic species occur with better regio- and enantioselectivity. [ABSTRACT FROM AUTHOR]
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- *CONFERENCES & conventions
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Details
- Language :
- English
- ISSN :
- 00334545
- Volume :
- 80
- Issue :
- 5
- Database :
- Academic Search Index
- Journal :
- Pure & Applied Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 33004272
- Full Text :
- https://doi.org/10.1351/pac200880050967