Effects of Solvent and Residual Water on Enhancing the Reactivity of Six-Membered Silyloxyallyl Cations toward Nucleophilic Addition
© 2016 American Chemical Society. 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.
Publication Source (Journal or Book title)
Malone, J., Cleveland, A., Fronczek, F., & Kartika, R. (2016). Effects of Solvent and Residual Water on Enhancing the Reactivity of Six-Membered Silyloxyallyl Cations toward Nucleophilic Addition. Organic Letters, 18 (17), 4408-4411. https://doi.org/10.1021/acs.orglett.6b02194