60211-19-0Relevant articles and documents
Oxidative Ring Expansion of Cyclobutanols: Access to Functionalized 1,2-Dioxanes
Lapez, Mara-A Marta-N,Jamey, Nicolas,Pinet, Alexis,Figadeìre, Bruno,Ferri, Laurent
supporting information, p. 1626 - 1631 (2021/03/08)
Cyclobutanols undergo an oxidative ring expansion with Co(acac)2 and triplet oxygen to give 1,2-dioxanols. The formation of an alkoxy radical drives the regioselective cleavage of the ring on the more substituted side before insertion of molecular oxygen. The reaction is particularly effective on secondary cyclobutanols but works also on certain tertiary alcohols. Further substitution with neutral nucleophiles under catalytic Lewis acid conditions led to original 1,2-dioxanes with a preferred 3,6-cis-configuration.
New efficient and stereoselective [2+2] cycloadditions of dimethylaluminum enolates with phenylvinylsulfoxide
Bienayme, Hugues,Guicher, Nathalie
, p. 5511 - 5514 (2007/10/03)
Lewis-acidic enolates, such as dimethylauminum enolates undergo cis-stereoselective [2+2] cycloadditions with phenylvinylsulfoxide. The method is quite general and gives good yields of synthetically valuable substituted cyclobutanols. The remaining sulfoxide handle can be further manipulated, giving access to diverse chemical functionalities.
