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Synthesis 2023; 55(20): 3402-3414
DOI: 10.1055/a-2092-9205
DOI: 10.1055/a-2092-9205
paper
Synthesis of 2,2-Disubstituted and 2,2,3-Trisubstituted 1,4-Dioxane-Derived Building Blocks
This work was funded by Enamine Ltd. and the Ministry of Education and Science of Ukraine [Grant Nos. 0121U100387 (21BF037-01M to B.V.V. and O.O.G.) and 0122U001962 (22BF037-02 to O.O.G.)]
Abstract
An approach to the preparation of 2,2-disubstituted and 2,2,3-trisubstituted 1,4-dioxane-derived building blocks is described. The reaction sequence commenced from dimethyl- or spirocyclobutyl-substituted oxiranes bearing an additional benzyloxy group as the starting materials. The key step of the 1,4-dioxane ring construction included oxirane ring opening with ethylene glycol monolithium salt, followed by the two-step cyclization of the diols obtained. The utility of the method was demonstrated by multigram preparation (up to 300 g; 30 g average scale of the final products) of 2,2-dimethyl-1,4-dioxane and 5,8-dioxaspiro[3.5]nonane building blocks, i.e. carboxylic acids, alcohols, amines, aldehyde, ketones, and bromides. Additional synthetic possibilities were shown by the preparation of selected examples of 1,4-dioxane-containing acetylenes, thiols, sulfonyl halides, and sulfonamides.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2092-9205.
- Supporting Information
Publikationsverlauf
Eingereicht: 20. Februar 2023
Angenommen: 12. Mai 2023
Accepted Manuscript online:
12. Mai 2023
Artikel online veröffentlicht:
02. August 2023
© 2023. Thieme. All rights reserved
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