1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

Bram Ryckaert; Ellen Demeyere; Frederick Degroote; Hilde Janssens; Johan M Winne

doi:10.3762/bjoc.19.12

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

Beilstein J Org Chem. 2023 Feb 2:19:115-132. doi: 10.3762/bjoc.19.12. eCollection 2023.

Authors

Bram Ryckaert¹, Ellen Demeyere¹, Frederick Degroote¹, Hilde Janssens¹, Johan M Winne¹

Affiliation

¹ Department of Organic and Macromolecular Chemistry, Ghent University, Krijgslaan 281 (S4), 9000 Gent, Belgium.

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)aromatic building blocks. 1,4-Dithianes have as yet not been investigated to the same extent as their well-known 1,3-dithiane counterparts, 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: 1,4-dithianes; 1,4-dithiins; 2,3-dihydro-1,4-dithiins; heterocycles; target synthesis.

Publication types

Review

Grants and funding

BR, ED and FD thank FWO-Vlaanderen for awarding them a predoctoral scholarship to conduct research in organic synthesis, including aspects of dithiane chemistry.