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

R Johnsson, D Olsson, U Ellervik

文献索引：Johnsson, Richard; Olsson, Dan; Ellervik, Ulf Journal of Organic Chemistry, 2008 , vol. 73, # 14 p. 5226 - 5232

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被引用次数: 29

摘要

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 11B NMR. The regioselectivity of borane reductions of cyclic acetals can be controlled by the choice of borane. Lewis acid activation of BH3· NMe3 increases the reaction rate and renders the borane the most electrophilic species, which ...