Sulfur-Based Chiral Iodoarenes: An Underexplored Class of Chiral Hypervalent Iodine Reagents

Mohamed Elsherbini; Arnaud Osi; Haifa Alharbi; Fatemah Karam; Thomas Wirth

doi:10.1055/a-1508-9593

Synthesis, Inhaltsverzeichnis

CC BY-NC-ND 4.0 · Synthesis 2023; 55(02): 307-314
DOI: 10.1055/a-1508-9593

paper

Special Issue dedicated to Prof. Alain Krief

Sulfur-Based Chiral Iodoarenes: An Underexplored Class of Chiral Hypervalent Iodine Reagents

Autoren

Mohamed Elsherbini

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK

^bNew address: Department of Chemistry, University of Huddersfield, Queensgate, Huddersfield HD1 3DH, UK
Arnaud Osi

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK
Haifa Alharbi

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK
Fatemah Karam

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK
Thomas Wirth ∗

^aSchool of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK

Abstract

Alle Artikel dieser Rubrik

Dedicated to Prof. Alain Krief on the occasion of his 80^th 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 derivatives

Volltext

Referenzen

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Zusatzmaterial

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