1,4-Dithianes : attractive C2-building blocks for the synthesis of complex molecular architectures
- Author
- Bram Ryckaert (UGent) , Ellen Demeyere (UGent) , Frederick Degroote (UGent) , Hilde Janssens (UGent) and Johan Winne (UGent)
- Organization
- Project
- Abstract
- This review covers the synthetic applications of 1,4-dithianes, as well as derivatives thereof at various oxidation states. The selected examples show how the specific heterocyclic reactivity can be harnessed for the controlled synthesis of carbon-carbon bonds. The reactivity is compared to and put into context with more common synthetic building blocks, such as 1,3-dithianes and (hetero)aro-matic building blocks. 1,4-Dithianes have as yet not been investigated to the same extent as their well-known 1,3-dithiane counter -parts, but they do offer attractive transformations that can find good use in the assembly of a wide array of complex molecular architectures, ranging from lipids and carbohydrates to various carbocyclic scaffolds. This versatility arises from the possibility to chemoselectively cleave or reduce the sulfur-heterocycle to reveal a versatile C2-synthon.
- Keywords
- Organic Chemistry, 1, 4-dithianes, 4-dithiins, 2, 3-dihydro-1, heterocycles, target synthesis, HETEROCYCLIC VINYL ETHERS, ASYMMETRIC TOTAL-SYNTHESIS, ETHANEDIYL S,S-ACETALS, ALLYL CATIONS, CYCLOADDITION, CHEMISTRY, ALPHA, REACTIVITY, ALCOHOLS, 5,6-DIHYDRO-1,4-DITHIINS
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Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-01H43QMR45QF6SZP36R9EKMJKX
- MLA
- Ryckaert, Bram, et al. “1,4-Dithianes : Attractive C2-Building Blocks for the Synthesis of Complex Molecular Architectures.” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 19, 2023, pp. 115–32, doi:10.3762/bjoc.19.12.
- APA
- Ryckaert, B., Demeyere, E., Degroote, F., Janssens, H., & Winne, J. (2023). 1,4-Dithianes : attractive C2-building blocks for the synthesis of complex molecular architectures. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 19, 115–132. https://doi.org/10.3762/bjoc.19.12
- Chicago author-date
- Ryckaert, Bram, Ellen Demeyere, Frederick Degroote, Hilde Janssens, and Johan Winne. 2023. “1,4-Dithianes : Attractive C2-Building Blocks for the Synthesis of Complex Molecular Architectures.” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 19: 115–32. https://doi.org/10.3762/bjoc.19.12.
- Chicago author-date (all authors)
- Ryckaert, Bram, Ellen Demeyere, Frederick Degroote, Hilde Janssens, and Johan Winne. 2023. “1,4-Dithianes : Attractive C2-Building Blocks for the Synthesis of Complex Molecular Architectures.” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 19: 115–132. doi:10.3762/bjoc.19.12.
- Vancouver
- 1.Ryckaert B, Demeyere E, Degroote F, Janssens H, Winne J. 1,4-Dithianes : attractive C2-building blocks for the synthesis of complex molecular architectures. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2023;19:115–32.
- IEEE
- [1]B. Ryckaert, E. Demeyere, F. Degroote, H. Janssens, and J. Winne, “1,4-Dithianes : attractive C2-building blocks for the synthesis of complex molecular architectures,” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 19, pp. 115–132, 2023.
@article{01H43QMR45QF6SZP36R9EKMJKX,
abstract = {{This review covers the synthetic applications of 1,4-dithianes, as well as derivatives thereof at various oxidation states. The selected examples show how the specific heterocyclic reactivity can be harnessed for the controlled synthesis of carbon-carbon bonds. The reactivity is compared to and put into context with more common synthetic building blocks, such as 1,3-dithianes and (hetero)aro-matic building blocks. 1,4-Dithianes have as yet not been investigated to the same extent as their well-known 1,3-dithiane counter -parts, but they do offer attractive transformations that can find good use in the assembly of a wide array of complex molecular architectures, ranging from lipids and carbohydrates to various carbocyclic scaffolds. This versatility arises from the possibility to chemoselectively cleave or reduce the sulfur-heterocycle to reveal a versatile C2-synthon.}},
author = {{Ryckaert, Bram and Demeyere, Ellen and Degroote, Frederick and Janssens, Hilde and Winne, Johan}},
issn = {{1860-5397}},
journal = {{BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY}},
keywords = {{Organic Chemistry,1,4-dithianes,4-dithiins,2,3-dihydro-1,heterocycles,target synthesis,HETEROCYCLIC VINYL ETHERS,ASYMMETRIC TOTAL-SYNTHESIS,ETHANEDIYL S,S-ACETALS,ALLYL CATIONS,CYCLOADDITION,CHEMISTRY,ALPHA,REACTIVITY,ALCOHOLS,5,6-DIHYDRO-1,4-DITHIINS}},
language = {{eng}},
pages = {{115--132}},
title = {{1,4-Dithianes : attractive C2-building blocks for the synthesis of complex molecular architectures}},
url = {{http://doi.org/10.3762/bjoc.19.12}},
volume = {{19}},
year = {{2023}},
}
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