Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 73, Issue 14, Pages 5226-5232Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo800396g
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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 (11)B NMR. The regioselectivity of borane reductions of cyclic acetals can be controlled by the choice of borane. Lewis acid activation of BH(3) center dot NMe(3) 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 BH(3) center dot THF.
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