Gold-Catalyzed Addition of Propargyl Acetates to Olefins via O-Acyl Migration/Cyclopropanation Sequence: Insight into the Diastereoselective Formation of the Alkene

This article discloses a study on the well-known addition of propargyl acetates to olefins via an O-acyl migration/ cyclopropanation sequence. Herein, we show that the stereochemical outcome of the olefin is strongly dependent on the gold catalyst and reaction parameters (concentration, temperature, and alkene partner equivalents); the E- and Z-isomers can be selectively formed by the judicious choice of reaction conditions.

Automated summary

This study reveals the importance of gold catalyst and reaction parameters in the addition of propargyl acetates to olefins via an O-acyl migration/ cyclopropanation sequence. The stereochemical outcome of the olefin can be selectively controlled by carefully choosing the reaction conditions, resulting in the formation of E- and Z-isomers.