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Reductive openings of acetals: Explanation of regioselectivity in borane reductions by mechanistic studies

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Author

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.

Publishing year

2008

Language

English

Pages

5226-5232

Publication/Series

Journal of Organic Chemistry

Volume

73

Issue

14

Document type

Journal article

Publisher

The American Chemical Society (ACS)

Topic

  • Organic Chemistry

Status

Published

ISBN/ISSN/Other

  • ISSN: 1520-6904