80359-96-2Relevant articles and documents
Tandem Rh-catalysis: Decarboxylative β-keto acid and alkyne cross-coupling
Cruz, Faben A.,Chen, Zhiwei,Kurtoic, Sarah I.,Dong, Vy M.
supporting information, p. 5836 - 5839 (2016/05/19)
Herein, we describe a regioselective Rh-catalyzed decarboxylative cross-coupling of β-keto acids and alkynes to access branched γ,δ-unsaturated ketones. Rh-hydride catalysis enables the isomerization of an alkyne to generate a metal-allyl species that can undergo carbon-carbon bond formation. Ketones are generated under mild conditions, without the need for base or activated electrophiles.
Iridium-catalyzed regioselective decarboxylative allylation of β-ketoacids: Efficient construction of γ,δ-unsaturated ketones
Chen, Shu-Jie,Lu, Guo-Ping,Cai, Chun
supporting information, p. 11512 - 11514 (2016/01/15)
A highly regioselective protocol for the direct synthesis of γ,δ-unsaturated ketones from β-ketoacids and allylic alcohols was proposed and accomplished relying on the combination of [Ir(cod)Cl]2 and 10-camphorsulfonic acid via decarboxylative allylation.
Ketal Claisen Rearrangements of Simple Aliphatic Ketals
Daub, G. William,McCoy, Mark A.,Sanchez, Michael G.,Carter, James S.
, p. 3876 - 3883 (2007/10/02)
The ketal Claisen rearrangement has been studied with eight simple unsymmetrical ketals in order to establish the regioselectivity associated with the transformation.Three different allylic alkohols were examined.Carbon-carbon bond formation on the more highly substituted branch of the parent ketone generally predominated over substitution on the less highly substituted branch.However, additional substituents on the α or β carbons of the ketal lower the selectivity substantially.Extensive β substitution can completely reverse the normal selectivity.The rection is relatively insensitive to the concentration of the weak acid catalyst.The yields range between 27 and 84 percent, and the products have been characterized.A model that accounts for the observations is also described.