Abstract
Chiral sulfinyl compounds, sulfoxides, sulfoximines, sulfinamides, and other derivatives, play an important role in asymmetric synthesis as versatile auxiliaries, ligands, and catalysts. They are also recognized as pharmacophores found in already marketed and well-sold drugs (e.g., esomeprazole) and used in drug design. This review is devoted to the modern methods of preparation of sulfinyl derivatives in enantiopure or enantiomerically enriched form. Selected new approaches leading to racemic products for which the asymmetric variant can be developed in the future are mentioned as well.
Highlights
Chiral sulfinyl compounds, sulfoxides, sulfoximines, sulfinamides, and other derivatives, play an important role in asymmetric synthesis as versatile auxiliaries, ligands, and catalysts
The present paper is, not a simple update of our previous article as we have decided to extend our interest to other important groups of chiral sulfinyl compounds, which are prepared in a stereoselective manner, e.g., sulfinamides, sulfinimines, sulfinates and thiosulfinates, sulfoximines, sulfonimidamides, and sulfonimidates
Enantioselective Oxidation Catalyzed by Titanium/(S,S)-Hydrobenzoin[48] sulfides were converted to the corresponding sulfoxides in high yield and with ee values up to 95%; the presence and placement of hydroxyl group was found crucial for the observed stereochemical outcome
Summary
The study of stereochemistry of organic sulfur compounds has a long and rich history.[16]. Three important papers concerning application of chiral sulfoxides in asymmetric catalysis have already been mentioned in the Introduction.[5−7] A general review by Maguire and co-workers on the synthesis of enantioenriched sulfoxides, with a special attention paid to kinetic resolution, was published in 2011.33 Several articles were devoted to asymmetric oxidations, including sulfoxidations, with a focus on environmentally benign methods.[34−36] A first part of a paper in which Franklin Davis described his “adventures in sulfur−nitrogen chemistry” (using his own words) described the preparation and use of chiral oxaziridine derivatives (known as Davis reagents) in enantioselective oxidation of sulfenyl compounds: sulfides, disulfides, and sulfenylimines.[37] In 2018, a review by Han et al was published, presenting the developments in the preparation of optically active sulfoxides in the years 2011−2016.38 An important issue of correct determination of stereochemical outcome of synthetic reactions has been discussed in detail. We shall focus on the main tendencies that could be observed in field in the past decade
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