Abstract
An approach to the preparation of 2-mono-, 2,2- and 2,3-disubstituted 1,4-dioxane
derivatives is described. The reaction sequence commences from readily available epoxides,
in most cases prepared via the Corey–Chaikovsky reaction of the corresponding aldehydes
and ketones. The key step of the method is epoxide ring opening with ethylene glycol
monosodium salt, followed by further cyclization of the diols obtained. The utility
of the approach was demonstrated by multigram preparation of novel functionalized
1,4-dioxanes bearing additional cycloalkane, piperidine or pyrrolidine rings, mostly
spirocyclic compounds, which are advanced building blocks for medicinal chemistry.
Key words
oxygen heterocycles - 1,4-dioxane - spiro compounds - building blocks - oxirane
