Recent Applications in the Use of Sulfoxides as Chiral Auxiliaries for the Asymmetric Synthesis of Natural and Biologically Active Products

Abstract

The contribution of chiral sulfoxides as versatile auxiliaries in the field of organic chemistry has shown a prevalent interest in the asymmetric synthesis of natural products during the last 45 years. In this short review, we report the recent applications of these chiral auxiliaries to the synthesis of natural and biological active products highlighted from 2010 to 2019. We hope to allow the reader to have an overview of the potential of sulfoxide chemistry in the field of enantio­selective synthesis.1 Introduction2 Diastereoselective Additions to Ketones2.1 Reduction of β-Keto Sulfoxides2.2 Reduction of β-Keto Sulfoxides Followed by Bromohydrin Forma tion3 Synthesis of an α-Amino α′-Sulfinyl Ketone Followed by Diastere oselective Reduction of the β-Keto Sulfoxide4 Diastereoselective Addition of Carbanionic Chiral Sulfoxides4.1 Addition to an Aldehyde4.1.1 Aldol Reactions4.1.2 Reformatsky-Type Reactions4.2 Additions to Chiral Sulfinimines5 Diastereoselective Cyclization Reactions Directed by a Chiral Sulf oxide5.1 1,4-Radical Additions5.2 Intramolecular Conjugate Additions5.3 Nazarov Cyclizations5.4 Diels–Alder Reactions6 Atropodiastereoselective Synthesis7 Conclusion

Deployment of Sulfinimines in Charge-Accelerated Sulfonium Rearrangement Enables a Surrogate Asymmetric Mannich Reaction

“…Enantioenriched organosulfur compounds have emerged as reagents of choice for stereoselective synthesis through chiral propagation . We herein show that, by synergistically combining enantioenriched sulfinimines in sulfonium rearrangements with the chemoselectivity of amide activation, a diastereo- and enantioselective strategy to access acyclic, polysubstituted β-amino amides results (Scheme C).…”

Electrochemical Bromofunctionalization of Alkenes and Alkynes—To Sustainability and Beyond

“…The electrochemical bromination and bromofunctionalization of alkenes are wellresearched areas, as their products serve as highly valuable synthetic intermediates and important chemicals. Vicinal dibromides, bromohydrins and bromoesters serve as useful intermediates for pharmaceuticals and fine chemicals [29,63]. Moreover, the halogenated species can be simply further functionalized resulting in a plethora of elaborated products.…”

Surfactant-controlled switchable oxygenation of sulfides to sulfoxides or sulfones under visible-light irradiation

“…The sulfones and sulfoxides, serving as crucial frameworks for a diverse array of natural products and pharmaceutically active molecules, have emerged as highly desirable targets in the field of organic chemistry. 1 Numerous bioactive molecules containing the basic configuration of sulfones or sulfoxides have been reported, 2 such as neosartoryone A, 3 sulindac, 4 vioxx, 5 mesotrione, 6 antifungal agents 7 and fenofibrate derivatives 8 (Scheme 1). In addition, sulfones and sulfoxides are also commonly used as versatile synthons in synthetic chemistry.…”