Effects of Solvent and Residual Water on Enhancing the Reactivity of Six-Membered Silyloxyallyl Cations toward Nucleophilic Addition

A new strategy for
the generation of six-membered unsymmetrical
silyloxyallyl cations using catalytic mild Brønsted acid is reported.
These reactive intermediates were found to readily undergo direct
nucleophilic addition with a broad range of nucleophiles to produce
various α,α′-disubstituted silyl enol ether structural
motifs. The findings also highlight the significance of the solvent
effect and residual water in enhancing the reaction rate.