Cover Feature: Asymmetric Direct/Stepwise Dearomatization Reactions Involving Hypervalent Iodine Reagents (Chem. Asian J. 4/2022)

Asymmetric Synthesis with Hypervalent Iodine Reagents.

This chapter describes recent developments in stereoselective synthesis using hypervalent iodine reagents.

Cyclic Hypervalent Iodine Reagents for Atom-Transfer Reactions: Beyond Trifluoromethylation.

Hypervalent iodine compounds are privileged reagents in organic synthesis because of their exceptional reactivity. Among these compounds, cyclic derivatives stand apart because of their enhanced stability. They have been widely used as oxidants, but their potential for functional-group transfer has only begun to be investigated recently. The use of benziodoxol(on)es for trifluoromethylation (To...

Stereoselective Ketone Rearrangements with Hypervalent Iodine Reagents.

The first stereoselective version of an iodine(III)-mediated rearrangement of arylketones in the presence of orthoesters is described. The reaction products, α-arylated esters, are very useful intermediates in the synthesis of bioactive compounds such as ibuprofen. With chiral lactic acid-based iodine(III) reagents product selectivities of up to 73 % ee have been achieved.

Hydrogen bonding and alcohol effects in asymmetric hypervalent iodine catalysis: enantioselective oxidative dearomatization of phenols.

Thioamination of Alkenes with Hypervalent Iodine Reagents

An efficient thioamination of alkenes mediated by iodine(III) reagents is described. The use of different sulfur nucleophiles allows the flexible synthesis of 1,2-aminothiols from alkenes. By employing chiral iodine(III) reagents, a stereoselective version of the thioamination protocol has also been developed.