Recent Application of Chiral Aryliodine Based on the 2-Iodo­resorcinol Core in Asymmetric Catalysis

Abstract

Chiral iodoarenes have been steadily increasing in importance in recent years, especially in enantioselective synthesis and catalysis. Since the development of the concept of chiral iodine(I/III) catalysis, the use of various chiral aryliodine frameworks has been explored in this area. This short review gives an overview of the use of chiral hypervalent iodine(I/III) reagents based on the 2-iodoresorcinol core with two attached two lactic side chains bearing ester or amide groups for the catalytic enantioselective dearomatization of phenol compounds, asymmetric oxidation of alkenes, and enantioselective α-functionalization of carbonyl compounds highlighting the excellent reactivities in terms of yield and enantioselectivity.1 Introduction2 Enantioselective Dearomatization of Phenol Derivatives3 Asymmetric Oxidation of Alkenes4 Enantioselective α-Functionalization of Carbonyl Compounds5 Conclusion and Outlook

Recent Developments in Enantioselective Organocatalytic Cascade Reactions for the Construction of Halogenated Ring Systems

“…Later, in 2014, Kita, Shibata and coworkers expanded this chemistry, but showed at the same time that a catalytic enantioselective intramolecular version was possible, using reagent generated in situ from catalytic amounts of a C 2 ‐symmetric ( R )‐binaphthyl diiodide C5 and stoichiometric amounts of MCPBA and obtained, in this way, from 15 , a fluorinated piperidine ( 16 ) in good ees (Figure 9). [64] Several examples of this chemistry have now been developed, and the majority has involved at least one intramolecular reaction and hence ring formation [65,66] …”

Introduction to hypervalent iodine chemistry. Part 3

“…62 The development of highly efficient, enantioselective molecular catalysts based on the unique redox and photoredox chemistry of iodine has been one of the most impressive recent achievements in the field of HI chemistry. 11,18,26,36,46,48,61 Numerous synthetic methodologies are based on the very useful oxidizing properties of HI reagents, combined with their benign environmental character and commercial availability. The use of hypervalent iodine species for the coupling reactions leading to new carbon-carbon bonds was surveyed in two reviews.…”

“…15,44,45,49,51,53,56 The HI based methodologies have found wide application in the synthesis of natural products. 25,41,44,48 Several recent reviews have been dedicated to synthetic applications of specific classes of hypervalent iodine compounds. Aryliodonium salts have attracted significant interest as electrophilic arylating reagents.…”

An Efficient Approach for 3,3-Disubstituted Oxindoles Synthesis: Aryl Iodine Catalyzed Intramolecular C–N Bond Oxidative Cross-Coupling

“…In the recent decade, aryl iodine catalyzed reactions have exhibited the great potential of rapidly obtaining heterocycles with structural complexity in a single transformation which is particularly significant for avoiding metal contamination in the preparation of molecules with medicinal relevance . However, construction of 3,3-disubstituted oxindole derivatives catalyzed by aryl iodine remains a difficult problem.…”