188359-88-8Relevant articles and documents
Mechanistic insights into the palladium-induced domino reaction leading to ketones from benzyl β-ketoesters: First characterization of the enol as an intermediate
Detalle, Jean-Francois,Riahi, Abdelkhalek,Steinmetz, Vincent,Henin, Francoise,Muzart, Jacques
, p. 6528 - 6532 (2004)
The monitoring by UV spectroscopy of the Pd-catalyzed hydrogenolysis in acetonitrile of 2-methyl-2-benzyloxycarbonyl-1-indanone and 2-methyl-2- benzyloxycarbonyl-1-tetralone showed the successive formation of corresponding β-ketoacids and enols to deliver finally the ketones. Some factors which influence the stability of the intermediates are determined. In contrast to the above benzyl β-ketoesters, the enol was not detected from benzyl (2-methylinden-3-yl) carbonate.
Structural effects in the Pd-induced enantioselective deprotection-decarboxylation of β-ketoesters
Kukula, Pavel,Matousek, Vaclav,Mallat, Tamas,Baiker, Alfons
, p. 2859 - 2868 (2008/09/17)
Structural effects in the chiral base and the influence of some key reaction parameters (catalyst type and solvent) in the Pd-induced enantioselective decarboxylation (cascade reaction) of three different α,α-disubstituted benzyl β-ketoesters were explored. The reaction intermediate after debenzylation (β-keto-carboxylic acid) was synthesized and its decarboxylation studied independently. The highest ee (up to 60%) in the cascade reaction was achieved with those substrates that contained an aromatic ring system and with chiral amino alcohols that possessed an extended aromatic ring (quinine and quinidine). Polar solvents with weak H-bond donor and acceptor properties favor enantioselection.
