Diastereoselective Access to 3-Aminoindanones Through Domino Approach

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Catalysis

Background:

• Stereoselective synthesis is crucial for developing complex organic molecules.
• 3-Aminoindanones are important structural motifs in medicinal chemistry.
• Efficient methods for constructing β-quaternary carbons are highly sought after.

Purpose of the Study:

• To develop a novel intermolecular approach for the stereoselective synthesis of 3-aminoindanones.
• To introduce a β-quaternary carbon center during the synthesis.
• To explore a catalytic system for this transformation.

Main Methods:

• Utilized a catalytic system comprising a silver salt and phosphoric acid.
• Employed 2-alkynylacetophenones and anilines as starting materials.
• Investigated reaction conditions for optimal yield and stereoselectivity.

Main Results:

• Achieved stereoselective synthesis of 3-aminoindanones bearing a β-quaternary carbon.
• Demonstrated moderate to good yields for a range of substrates.
• Exhibited excellent diastereoselectivity and broad functional group tolerance.
• Successfully scaled up the reaction and performed further synthetic transformations.

Conclusions:

• The developed catalytic system provides an efficient route to valuable 3-aminoindanones.
• The protocol shows significant synthetic utility and potential for further applications.
• This method advances the stereoselective synthesis of complex organic structures.