Sulfur ylides in the synthesis of heterocyclic and carbocyclic compounds

2 Synthetic methods : Part (iv) Heteroatom methods

“…28 Other organosulfur reviews published in 2001 include: rearrangements of sulfoxides and sulfones in total synthesis, 29 the chemistry of acetylenic and allenic sulfones, 30 and the use of sulfonium ylides in the synthesis of carbocyclic and heterocyclic compounds. 31 The application of sulfur ylides to asymmetric epoxidation, aziridination and cyclopropanation was a vibrant area of research during 2001. These reactions were first reported, in achiral form, by Corey and Chaykoysky and are sometimes named after them.…”

Asymmetric transformations from sulfoxonium ylides

“…Epoxidation, aziridination, cyclopropanation, Steven's rearrangements and sigmatropic rearrangements are the main classical reactions that have been established for the sulfur ylides (Scheme 2A-C). 18,19 In the last few decades, sulfoxonium ylides have regained the attention of many researchers and those in the industry, particularly owing to their ability to generate carbene species, a eld that was for a long time dominated by diazo compounds. Metal-carbenes from sulfoxonium ylides have been employed in several insertion reactions, such as into X-H (N, O, S, B, P) and C-H bonds (Scheme 2D and E).…”

Sulfoxonium and Sulfonium Ylides as Diazocarbonyl Equivalents in Metal‐Catalyzed Insertion Reactions

“…Sulfur ylides12,19 are typical carbanions with a neighboring positive sulfur atom. Their stabilities depend on the electron delocalization of the carbanionic center and on the substitution on the sulfur atom.…”

“…The first stable sulfur ylides were described in 1930 by Ingold and Jes-sop, [13] but it was after the pioneering work of Johnson and LaCount, [14] Franzen, [15] and Corey and Chaykovsky [16][17][18] (dimethylsulfonium and dimethylsulfoxonium ylides) that they received more attention. Sulfur ylides [12,19] are typical carbanions with a neighboring positive sulfur atom. Their stabilities depend on the electron delocalization of the carbanionic center and on the substitution on the sulfur atom.…”