473758-19-9Relevant academic research and scientific papers
Palladium-catalysed alkene chain-running isomerization
Kocen, Andrew L.,Brookhart, Maurice,Daugulis, Olafs
, p. 10010 - 10013 (2017)
We report a method for palladium-catalysed chain-running isomerization of terminal and internal alkenes. Using an air-stable 2,9-dimethylphenanthroline-palladium catalyst in combination with NaBAr4 promoter, olefins are converted to the most stable double bond isomer at -30 to 20 °C. Silyl enol ethers are readily formed from silylated allylic alcohols. Fluorinated substituents are compatible with the reaction conditions, allowing the synthesis of fluoroenolates. Catalyst loading as low as 0.05% can be employed on a gram scale.
Cyclopropanation of protected chiral, acyclic allylic alcohols: Expedient access to the anti-cyclopropylcarbinol derivatives
Charette, Andre B.,Lacasse, Marie-Christine
, p. 3351 - 3353 (2007/10/03)
(matrix presented) The diastereoselective cyclopropanation of silyl-protected chiral allylic alcohols using Shi's carbenoid (TFA-Et2Zn-CH2I2) gave access to the anti-cyclopropylcarbinyl silyl ethers with excellent diastereocontrol. The level of stereocontrol was shown to depend on the sizes of the protective group and the allylic substituent.
