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

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.

Automated summary

Chiral hypervalent iodine reagents play an important role in modern stereoselective organic synthesis. Although structurally diverse chiral hypervalent iodine reagents have been synthesized and extensively studied, hypervalent iodine reagents containing a chiral sulfur stereogenic center are rare and difficult to synthesize. In this study, a small library of iodoarenes containing chiral sulfinamide and chiral sulfoximine moieties was synthesized. The oxidation of chiral iodoarene precursors to iodine(III) reagents was challenging due to facile overoxidation of the sulfoxide moiety and loss of chirality. However, oxidation of chiral sulfonimidoyl derivatives was successful and led to novel sulfur-based chiral iodine(III) reagents.