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.