2023
DOI: 10.3762/bjoc.19.12
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1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

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-dithian… Show more

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Cited by 4 publications
(5 citation statements)
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“…Lewis acids in combination with dithioallyl alcohol 1 generally gave poor results for the cyclopentannulation of styrene as this gave complex mixtures. The most promising reactions were those with gallium( iii )triflate and zinc( ii )bromide, 14,15 but these still gave low isolated yields for the expected adduct 2a compared to the reference experiment with trifluoroacetic acid (Table 1, entries 1–3). The combination of the silyl ether 12 with gallium( iii )triflate gave a relatively clean reaction, 15 a but the isolated yield was again low (entry 4).…”
Section: Resultsmentioning
confidence: 99%
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“…Lewis acids in combination with dithioallyl alcohol 1 generally gave poor results for the cyclopentannulation of styrene as this gave complex mixtures. The most promising reactions were those with gallium( iii )triflate and zinc( ii )bromide, 14,15 but these still gave low isolated yields for the expected adduct 2a compared to the reference experiment with trifluoroacetic acid (Table 1, entries 1–3). The combination of the silyl ether 12 with gallium( iii )triflate gave a relatively clean reaction, 15 a but the isolated yield was again low (entry 4).…”
Section: Resultsmentioning
confidence: 99%
“…14 An attractive feature of this methodology is that the obtained cyclopentanoids like 2a or 2b can be chemoselectively transformed into a cyclopentene, via hydrodesulfurization. 15 Thus, the dithioallyl alcohol serves as a synthetic equivalent of a ‘naked’ allyl cation, opening up attractive options in synthesis.…”
Section: Introductionmentioning
confidence: 99%
“…This isomer can then be chemoselectively hydrodesulfurized with Raney nickel to give attractive cyclopentene synthetic intermediate 13 . This transformation underscores the advantage of the 1,4-dithiane moiety . Hydroboration of the alkene in 7a gave a regio- and stereoselective conversion to the fully substituted cyclopentane 14 with control over the relative stereochemistry of all five stereocenters.…”
mentioning
confidence: 75%
“…This transformation underscores the advantage of the 1,4-dithiane moiety. 10 Hydroboration of the alkene in 7a gave a regio-and stereoselective conversion to the fully substituted cyclopentane 14 with control over the relative stereochemistry of all five stereocenters. Finally, when product 7a is resubjected to the same conditions of its own synthesis, it undergoes a swift and fully stereoselective vinylcyclopropanation reaction with 3 to give 15 as a single diastereomer.…”
mentioning
confidence: 99%
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