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

Marion Barbazanges (1, 2) , Yves Gimbert (1) , Louis Fensterbank (1)

1 IPCM - Institut Parisien de Chimie Moléculaire
2 CASCH - CAtalysis and Sustainable CHemistry

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, alkene partner equivalents); E and the Z isomers can be selectively formed by judicious choice of reaction conditions.

Mots clés: cycloisomerization; diastereoselectivity; gold; cyclopropane

Domaines: Catalyse; Chimie organique

Marion Barbazanges, Yves Gimbert, Louis Fensterbank. Gold-Catalyzed Addition of Propargyl Acetates to Olefins via O -Acyl Migration/Cyclopropanation Sequence: Insight into the Diastereoselective Formation of the Alkene. Journal of Organic Chemistry, 2023, 88 (5), pp.3297-3302. ⟨10.1021/acs.joc.2c02623⟩. ⟨hal-04178887⟩