36321-95-6Relevant articles and documents
A facile generation of enolates from silyl enol ethers by potassium ethoxide
Yu, Wensheng,Jin, Zhendong
, p. 369 - 372 (2007/10/03)
Cyclic silyl enol ethers were successfully cleaved by EtOK to generate the corresponding enolates. Reactions with EtOK were faster and the corresponding enolates could be trapped by electrophiles and oxidants to give the kinetic products exclusively.
REGIOSELECTIVE ALLYLATION OF KETONES
Cormier, Russell A.,Morris, Theresa E.
, p. 1673 - 1676 (2007/10/02)
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Palladium-Catalyzed Decarboxylative Allylic Alkylation of Allylic Acetates with β-Keto Acids
Tsuda, Tetsuo,Okada, Masahiro,Nishi, Sei-ichi,Saegusa, Takeo
, p. 421 - 426 (2007/10/02)
In the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium, β-keto acids react with allylic acetates at ambient temperature to produce α-allylic ketones in good yields with quantitative decarboxylation.This palladium-catalyzed decarboxylative allylic alkylation of allylic acetates with β-keto acids is characterized by high regio- and stereoselectivity.Allylation of β-keto acid takes place at the carbon atom bearing a carboxyl group.Allylic alkylation of allylic acetate with β-keto acid occurs at the less substituted end of the allyl group.The resultant carbon-carbon double bond of the α-allylic ketone has the E configuration.Allylic alkylation of lactone 25 with benzoylacetic acid proceeds preferably with retention of configuration, indicative of trans attack of the enolate on the (?-allyl)palladium intermediate from the opposite side of palladium even in the coexistence of free carboxylic acids.