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DOI: 10.1055/a-1508-9593
Sulfur-Based Chiral Iodoarenes: An Underexplored Class of Chiral Hypervalent Iodine Reagents
We are grateful to the Erasmus program for the financial support and a scholarship to A.O. We thank the government of Saudi Arabia and the Northern Borders University, KSA, for the financial support and scholarship to H.A. The authors are grateful to School of Chemistry, Cardiff University, for the financial support and facilities.
Dedicated to Prof. Alain Krief on the occasion of his 80th birthday
Abstract
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.
Key words
hypervalent iodine - oxidation - stereoselective synthesis - sulfoximines - sulfur derivativesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1508-9593.
- Supporting Information
Publication History
Received: 01 April 2021
Accepted after revision: 14 May 2021
Accepted Manuscript online:
14 May 2021
Article published online:
14 June 2021
© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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