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1 article(s) from Winne, Johan M

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

Bram Ryckaert,
Ellen Demeyere,
Frederick Degroote,
Hilde Janssens and
Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

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Graphical Abstract

Scheme 1: 1,3-Dithianes as useful synthetic building blocks: a) general synthetic utility (in Corey–Seebach-t...

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Scheme 2: Metalation of other saturated heterocycles is often problematic due to β-elimination [16,17].

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Scheme 3: Thianes as synthetic building blocks in the construction of complex molecules [18].

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Figure 1: a) 1,4-Dithiane-type building blocks that can serve as C2-synthons and b) examples of complex targe...

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Scheme 4: Synthetic availability of 1,4-dithiane-type building blocks.

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Scheme 5: Dithiins and dihydrodithiins as pseudoaryl groups [36-39].

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Scheme 6: Metalation of other saturated heterocycles is often problematic due to β-elimination [40-42].

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Figure 2: Reactive conformations leading to β-fragmentation for lithiated 1,4-dithianes and 1,4-dithiin.

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Scheme 7: Mild metalation of 1,4-dithiins affords stable heteroaryl-magnesium and heteroaryl-zinc-like reagen...

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Scheme 8: Dithiin-based dienophiles and their use in synthesis [33,49-54].

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Scheme 9: Dithiin-based dienes and their use in synthesis [55-57].

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Scheme 10: Stereoselective 5,6-dihydro-1,4-dithiin-based synthesis of cis-olefins [42,58].

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Scheme 11: Addition to aldehydes and applications in stereoselective synthesis.

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Figure 3: Applications in the total synthesis of complex target products with original attachment place of 1,...

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Scheme 12: Direct C–H functionalization methods for 1,4-dithianes [82,83].

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Scheme 13: Known cycloaddition reactivity modes of allyl cations [84-100].

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Scheme 14: Cycloadditions of 1,4-dithiane-fused allyl cations derived from dihydrodithiin-methanol 90 [101-107].

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Scheme 15: Dearomative [3 + 2] cycloadditions of unprotected indoles with 1,4-dithiane-fused allyl alcohol 90 [30]....

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Scheme 16: Comparison of reactivity of dithiin-fused allyl alcohols and similar non-cyclic sulfur-substituted ...

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Scheme 17: Applications of dihydrodithiins in the rapid assembly of polycyclic terpenoid scaffolds [108,109].

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Scheme 18: Dihydrodithiin-mediated allyl cation and vinyl carbene cycloadditions via a gold(I)-catalyzed 1,2-s...

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Scheme 19: Activation mode of ethynyldithiolanes towards gold-coordinated 1,4-dithiane-fused allyl cation and ...

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Scheme 20: Desulfurization problems.

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Scheme 21: oxidative decoration strategies for 1,4-dithiane scaffolds.

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Review

Published 02 Feb 2023

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