Synthesis of functionalized tetrahydropyransviacascade cycloaddition involving silyloxyallyl cation intermediates
© The Royal Society of Chemistry 2020. An expedient synthesis of highly substituted tetrahydrobenzofuranviaan unsymmetrical silyloxyallyl cation is reported. Conveniently generated under catalytic Brønsted acid conditions, nucleophilic capture of this reactive intermediate by silylenolate, followed by Paal-Knorr cascade cyclization in the presence of tosic acid monohydrate effectively constructed the tetrahydrobenzofuran core in a single synthetic step.
Publication Source (Journal or Book title)
Badmus, F., Malone, J., Fronczek, F., & Kartika, R. (2020). Synthesis of functionalized tetrahydropyransviacascade cycloaddition involving silyloxyallyl cation intermediates. Chemical Communications, 56 (37), 5034-5037. https://doi.org/10.1039/d0cc01796e