American Chemical Society
ol6b02194_si_002.cif (18.05 kB)

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

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posted on 2016-08-18, 19:34 authored by Joshua A. Malone, Alexander H. Cleveland, Frank R. Fronczek, Rendy Kartika
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.