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Sulfur-based chiral iodoarenes: an underexplored class of chiral hypervalent iodine reagents

Elsherbini, Mohamed, Osi, Arnaud, Alharbi, Haifa, Karam, Fatemah and Wirth, Thomas ORCID: 2021. Sulfur-based chiral iodoarenes: an underexplored class of chiral hypervalent iodine reagents. Synthesis: Journal of Synthetic Organic Chemistry 53 , A-H. 10.1055/a-1508-9593

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Chiral hypervalent iodine reagents are active players in modern stereoselective organic synthesis. Structurally diverse chiral hypervalent iodine reagents have been synthesised and extensively studied, but hypervalent iodine reagents containing chiral sulfur stereogenic centre are scarce and their synthesis is challenging. A small library of iodoarenes containing chiral sulfinamide and chiral sulfoximine moieties has been synthesised using commercially available reagents. The oxidation of the chiral iodoarene precursors to iodine(III) reagents was cumbersome due to facile overoxidation of the sulfoxide moiety and hence loss of chirality under various oxidation conditions. Oxidation of chiral sulfonimidoyl derivatives to the corresponding hypervalent iodine reagents was successful and led to novel sulfur-based chiral iodine(III) reagents.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Additional Information: This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License
Publisher: Thieme Gruppe
ISSN: 0039-7881
Date of First Compliant Deposit: 21 May 2021
Date of Acceptance: 14 May 2021
Last Modified: 29 Nov 2022 13:43

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