Chiral Organosulfur Compounds

Self-disproportionation of enantiomers (SDE) of chiral sulfur-containing compounds via achiral chromatography

“…Great interest in the synthesis of optically active sulfoxides [69][70][71][72][73] results at least from two reasons. First of all they are recognized as valuable and efficient reagents in synthetic chemistry, particularly for asymmetric synthesis due to high asymmetric induction exerted by a sulfinyl fragment, and its configurational stability.…”

“…First of all they are recognized as valuable and efficient reagents in synthetic chemistry, particularly for asymmetric synthesis due to high asymmetric induction exerted by a sulfinyl fragment, and its configurational stability. 69,71,[74][75][76] Several review articles are devoted to this topic. [77][78][79][80][81][82][83][84] Moreover, sulfoxides are present in many natural products and they play an important role in biology.…”

“…Despite the great advances in searching for more efficient procedures for asymmetric oxidation of sulfides, these protocols allow, as a rule, isolation of a mixture enriched in one enantiomer. [69][70][71][72][73]77,78 However, the optical purification of scalemic sulfoxides as an approach to enantiomerically pure products is still problematic, because results may not always be forthcoming. Therefore the studies devoted to the SDE phenomenon in the liquid phase in the family of optically active sulfoxides are very timely and their results should be very helpful in solving the limitations of this approach for the isolation of enantiomerically pure sulfoxides.…”

Methionine and derivatives: Exploring chirality at sulfur

“…A fact that usually receives little attention in the teaching of biochemistry/molecular biology is that some compounds derived from Met contain a chiral sulfur atom: they are S-adenosylmethionine and related materials (sulfonium salts), Met-S-oxide (a sulfoxide) and Met sulfoximine. Chiral sulfur compounds have long been of interest to organic chemists [2], being first described more than a century ago. As with chiral carbon compounds, enantioselective and diastereoselective interactions can occur with other chiral substances such as enzymes and receptors, thus influencing physiological events.…”

Stabilizing effect of intramolecular lewis base toward racemization of optically active selenoxides

“…Among tricoodinated organosulfur compounds, many optically active sulfoxides were synthesized and isolated, and their structures and reactions have been studied [1][2][3]. Moreover, asymmetric reactions utilizing optically active sulfoxide as a chiral source are becoming a very important technique in recent asymmetric synthesis [4,5]. The formation of optically active selenoxides is also proposed as a key intermediate in asymmetric synthesis, e.g.…”