Conversion and degradation pathways of sulfoximines

Abstract

The overview describes laboratory transformations leading to sulfoximine degradations to enable more focussed analyses of potential products and pathways.

Rediscovering Sulfinylamines as Reagents for Organic Synthesis

“…For preparative‐scale chemistry, enantioenriched sulfinamides are generally made starting from chiral menthyl sulfinate esters ( via resolution of diastereomers), [39] or more recently from stereospecific de‐alkylation of S ‐ tert ‐butylsulfoximines (often made from commercially available tert ‐butanesulfinamide). [ 40 , 41 , 42 ] Other ways to access enantioenriched sulfur(VI) compounds are also appearing in the literature, including other chiral auxiliary approaches, [43] kinetic resolution[ 44 , 45 ] and enantioselective desymmetrisation [46] of sulfoximines. However, the possibility of more direct approaches combining sulfinylamines with the many chiral Lewis acids and bases, organocatalysts, ligands and metal catalysts that have been developed in recent decades will surely not evade the attention of synthetic chemists for much longer.…”

Syntheses and Transformations of Sulfoximines

“…Understanding the potential pathways by which sulfoximines are degraded is critical in fields related to pharmaceutical and agricultural chemical applications. Sulfoximines have been degraded in the laboratory by subjecting them to chemical transformations, including reduction, oxidation, and C−S bond cleavage reactions [114] …”

Regio‐ and Stereoselective Chloro Sulfoximidations of Terminal Aryl Alkynes Enabled by Copper Catalysis and Visible Light

“…Undoubtfully, analogous addition reactions of sulfoximidoyl chlorides 4 to alkynes 2 are of interest as they should lead to specifically substituted vinyl sulfoximines 5 with numerous potential applications in organic synthesis. [9,10] Realizing this opportunity, we decided to investigate such transformations and report the first results here.…”

“…Substituting CuCl 2 by NiCl 2 and PdCl 2 proved ineffective (Table 1, entries 8 and 9). Other copper salts led to product formation, but generally, the yield of 5 a was lower than with CuCl 2 (Table 1, entries [10][11][12][13][14]. The only exception was copper(I) chloride which gave 5 a in 65% yield (Table 1, entry 11).…”