Applications of Catalytic Asymmetric Sulfide Oxidations to the Syntheses of Biologically Active Sulfoxides

Abstract

Optically active sulfoxides are important compounds for medicinal and pharmaceutical chemistry. Driven by the increasing demand for efficient, selective and environmentally friendly industrial processes, several catalytic methodologies have been developed in recent years for the stereoselective oxidation of sulfides for the preparation of biologically active sulfoxides. Both small-scale approaches to the problem as well as some large-scale applications that are already in industrial use are described in this review.

Porphyrins as Catalysts in Scalable Organic Reactions

“…Historically, sulfur-containing compounds have figured as targets for their importance to the pharmaceutical industry as antibacterial agents [25]. Therefore, the development of catalytic systems for the preparation of optically active sulfoxides is important, because they are chiral synthons [50] in the synthesis of bioactive compounds [51].…”

4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB as an oxidative biocatalyst in the synthesis of optically active sulfoxides

“…1,2 The oxidation of sulfides is the most straightforward method for the synthesis of sulfoxides and a great number of reagents are available for this reaction. [1][2][3] Also the enzymes are able to catalyze the enantioselective oxidation of sulfides, in processes carried out in water under mild reaction conditions. This makes a biocatalytic approach environmentally friendly and most appealing for industrial applications.…”

Synthesis of (R)-Modafinil via Organocatalyzed and Non-Heme Iron-Catalyzed Sulfoxidation Using H2O2 as an Environmentally Benign Oxidant

“…Being of medicinal interest, chiral sulfoxides serve as building blocks for the generation of biologically active compounds [2]. With the discovery of their presence in naturally chiral sulfoxide metabolites [3], such as cysteine sulfoxide derivatives, the demand for new synthetic routes was steadily growing, especially since the pioneering work of Kagan and Modena [4][5][6].…”

“…There are several examples that playing an important role in medicinal and pharmaceutical chemistry [2], including Esomeprazole [7,8], which acts as proton-pump inhibitor; the selective NK2 antagonist ZD7944 [9]; and the anti-cancer agent Sulindac ® (Figure 1) [10]. Modafinil (also known as Provigil ® [11], Figure 2), another important sulfoxide, is administered as a drug against narcolepsy [12] with significant advantages compared to dexamphetamine [13] and several other stimulants [14] because of a lower abuse potential [15,16].…”

“…There are several examples that playing an important role in medicinal and pharmaceutical chemistry [2], including Esomeprazole [7,8], which acts as proton-pump inhibitor; the selective NK 2 antagonist ZD7944 [9]; and the anti-cancer agent Sulindac ® (Figure 1) [10].…”