1-Arylallyloxysilanes as Formal Precursors to Potassium Homoenolate Equivalents of Ketones

20 March 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

This paper reports the successful conversion of 1-arylallyloxysilanes into highly nucleophilic siloxyallylpotassium intermediates using (trimethylsilyl)methylpotassium as the base. These organopotassium species react regioselectively with various electrophiles, leading to the formation of the corresponding 3-functionalized (Z)-silyl enol ethers. The resulting silyl enol ethers can undergo a range of α-functionalization reactions, yielding ketones with diverse structures. Thus, our method enables the effective utilization of 1-arylallyloxysilanes as formal precursors to potassium homoenolate equivalents of ketones.

Keywords

potassium
allyloxysilanes
silyl enol ethers
ketones
homoenolates
siloxyallylpotassiums

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General information, experimental procedures, computational study, characterization data, and NMR spectra.
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