Sulfoxonium ylides: simple compounds with chameleonic reactivity

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Sulfur ylides, first reported in 1930, gained prominence in the 1960s for strained ring synthesis.
• Recent growth in sulfur ylide chemistry is linked to similarities with diazo compound reactivity.

Purpose of the Study:

• To review the diverse reactions of sulfoxonium ylides.
• To compare sulfoxonium ylide chemistry with sulfonium ylides and diazo compounds.
• To highlight catalytic asymmetric methodologies.

Main Methods:

• Overview of literature on sulfur ylide reactions.
• Comparative analysis of sulfoxonium, sulfonium, and diazo compound reactivity.
• Focus on insertion, cyclization, and ring-opening reactions.

Main Results:

• Sulfoxonium ylides exhibit a broad range of synthetic transformations.
• Key reactions include insertions, cyclizations, and ring-opening processes.
• Catalytic asymmetric methods are increasingly important in sulfoxonium ylide chemistry.

Conclusions:

• Sulfoxonium ylides are versatile reagents in organic synthesis.
• Their reactivity profile offers alternatives to diazo compounds.
• Asymmetric catalysis significantly expands their synthetic utility.