Reductive openings of acetals: Explanation of regioselectivity in borane reductions by mechanistic studies
Research output: Contribution to journal › Article
The mechanisms of regioselective reductive openings of acetals were investigated in several model systems by a combination of Hammett plots, kinetic experiments, density functional calculations, and B-11 NMR. The regioselectivity of borane reductions of cyclic acetals can be controlled by the choice of borane. Lewis acid activation of BH3 center dot NMe3 increases the reaction rate and renders the borane the most electrophilic species, which associates to the more electron-rich oxygen of the acetal. In contrary, without activation, the regioselectivity is instead directed by the Lewis acid, as exemplified by the reaction with BH3 center dot THF.
|Research areas and keywords||
Subject classification (UKÄ) – MANDATORY
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 2008|
The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240)