A gold-catalysed fully intermolecular oxidation and sulfur-ylide formation sequence on ynamides

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Quaternary carbons are important structural motifs in many pharmaceuticals and natural products.
• Efficient methods for constructing sulfur-substituted quaternary carbons are highly sought after in organic synthesis.

Purpose of the Study:

• To develop a novel and efficient synthetic strategy for accessing sulfur-substituted quaternary carbons.
• To utilize ynamides as versatile building blocks in a three-component reaction.

Main Methods:

• Employing ynamides as diazo-equivalents in a three-component reaction.
• Utilizing chemoselective oxidation and intermolecular ylide formation to achieve [2,3]-sigmatropic rearrangements.
• Establishing a C-O, C-S, and C-C bond-forming sequence.

Main Results:

• Successful synthesis of functionalized compounds bearing sulfur-substituted quaternary carbons.
• Demonstration of an efficient and chemoselective reaction pathway.
• Ynamides effectively serve as diazo-equivalents in the described transformation.

Conclusions:

• The developed method provides a powerful new route to sulfur-substituted quaternary carbons.
• This approach offers a versatile platform for the synthesis of complex organic molecules.
• The use of ynamides as diazo-equivalents opens new avenues in sigmatropic rearrangement chemistry.