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摘要
The molecular mechanism and stereoselectivity of the BF3 Lewis acid catalyzed [3 + 2] cycloaddition (32CA) reaction between C-methoxycarbonyl nitrone and cyclopentene has been theoretically studied using DFT methods at the MPWB1K/6-31G(d) computational level. The BF3 catalyst accelerates the 32CA reaction by decreasing the activation energy leading to the formation of the trans cycloadduct as the kinetic product, in agreement with the experimental data. Inclusion of solvent effects slightly increases the activation energy and decreases the exothermic character of the 32CA reaction as a consequence of a better solvation of nitrone than the transition state and the cycloadduct. The use of the lithium cation as LA catalyst does not make any remarkable change with respect to the BF3 catalyzed process. The nature of the mechanism has been also studied using the reactivity indices defined within the conceptual DFT.
- 出版日期2015
