Recently, Kartika et al. have discovered a method for the regioselective addition of indole to unsymmetrical silyloxyallyl cations in which the indole would form a bond at the less substituted α’ carbon. The regioselectivity was thought to be dependent on the protecting group of the oxyallyl cation. DFT calculations were performed for the addition of indole to two oxyallyl cations, one containing a methyl protecting group which saw no regioselectivity, and one containing TBS which has been seen experimentally to selectively bind at the less substituted α’ carbon. These calculations yielded relative energetics as well as reaction pathways to help determine the factors driving the regioselectivity. Additionally, the effect of charge, p-orbital overlap, steric effects, and the stabilization due to water were analyzed and will be presented in detail.

DFT investigations on the regioselectivity of indole addition to unsymmetrical silyloxyallyl cations

2019 Spring National Meeting

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