Work

Gold(I)‐Catalyzed Enantioselective Cycloisomerization of 1,6‐Oxygenated Enynes: An Entry to Hedonic Derivatives

Year: 2025

Type: article

Abstract: A highly efficient gold(I)‐catalyzed enantioselective cycloisomerization of readily available 1,6‐oxygenated enynes is reported, enabling direct access to valuable 3‐oxabicyclo[4.1.0]hept‐4‐ene scaffolds with excellent enantiomeric excesses (up to >99% ee, 35 derivatives), in the presence of a chiral cationic Au(I) catalyst ((S)‐DTBM‐MeOBIPHEP(AuCl)2 /AgOTf system) in toluene. This methodology uniquely combines high stereoselectivity with good to excellent yields for volatile substrates that have been challenging derivatives in the asymmetric cycloisomerization community. Notably, the resulting chiral bicyclic ethers serve as versatile intermediates for the synthesis of novel hedonic derivatives. A systematic investigation of their odor profiles reveals remarkable differences between enantiomers, demonstrating the profound impact of molecular chirality on olfactory perception.

Source: Advanced Synthesis & Catalysis

DOI: 10.1002/adsc.70106

Authors: Anne Clisson, Véronique Michelet

Institutions: Centre National de la Recherche Scientifique, Université Côte d'Azur, Institut de Chimie de Nice

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,650

Funders: Centre National de la Recherche Scientifique, Sorbonne Université