403609-67-6Relevant academic research and scientific papers
Lewis acid/CpRu dual catalysis in the enantioselective decarboxylative allylation of ketone enolates
Linder, David,Austeri, Martina,Lacour, Jerome
supporting information; scheme or table, p. 4057 - 4061 (2009/12/06)
The addition of a Lewis acidic metal triflate salt Mg(OTf)2 as co-catalyst in the CpRu-catalyzed decarboxylative allylation of in situ-generated ketone enolates allows the reaction to proceed at lower temperature with higher regio- and enantios
Enantioselective CpRu-catalyzed carroll rearrangement - Ligand and metal source importance
Linder, David,Buron, Frederic,Constant, Samuel,Lacour, Jerome
supporting information; experimental part, p. 5778 - 5785 (2009/06/18)
The addition of unstabilized carbonyl nucleophiles to unsymmetrical allyl-metal fragments still represents a challenge to generate stereogenic centers enantio- and regioselectively. In this context, the decarboxylative Carroll rearrangement of allyl β-keto esters is particularly interesting, since chiral γ,δ-unsaturated ketones are obtained. Herein, we show that CpRu half-sandwich complexes can, with selected enantio-pure pyridine-monooxazoline ligands, catalyze this transformation and afford complete conversions along with good levels of regioselectivity and enantioselectivity. Even more challenging (electron-poor) substrates react (up to 86% ee, branched/linear ratio ≥ 97:03). In addition, the use of an air-stable metal precursor, namely [CpRu(η6-naphthalene)][PF6], allows the reaction to be carried out reproducibly even in non-anhydrous THF with a catalyst loading as low as 2 mol-%. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
