Reductive openings of acetals: Explanation of regioselectivity in borane reductions by mechanistic studies
Författare
Summary, in English
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.
Avdelning/ar
Publiceringsår
2008
Språk
Engelska
Sidor
5226-5232
Publikation/Tidskrift/Serie
Journal of Organic Chemistry
Volym
73
Issue
14
Dokumenttyp
Artikel i tidskrift
Förlag
The American Chemical Society (ACS)
Ämne
- Organic Chemistry
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 1520-6904