UNIGE document Scientific Article
previous document  unige:8007  next document
add to browser collection
Title

Enantio- and Regioselective CpRu Catalyzed Carroll Rearrangement

Authors
Müller, Jessica
Published in Pure and Applied Chemistry. 2008, vol. 80, no. 5, p. 967-977
Abstract The 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.
Keywords Allyl complexesEnantioselective catalysisHexacoordinated phosphorusN ligandsRuthenium
Identifiers
Note 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14). - Nara (Japan). - 2–6 August 2007
Full text
Article - document accessible for UNIGE members only Limited access to UNIGE
Structures
Citation
(ISO format)
AUSTERI, Martina et al. Enantio- and Regioselective CpRu Catalyzed Carroll Rearrangement. In: Pure and Applied Chemistry, 2008, vol. 80, n° 5, p. 967-977. https://archive-ouverte.unige.ch/unige:8007

200 hits

4 downloads

Update

Deposited on : 2010-06-21

Export document
Format :
Citation style :