Gold-Catalyzed Addition of Propargyl Acetates to Olefins via O -Acyl Migration/Cyclopropanation Sequence: Insight into the Diastereoselective Formation of the Alkene - Sorbonne Université Access content directly
Journal Articles Journal of Organic Chemistry Year : 2023

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

Abstract

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.
Fichier principal
Vignette du fichier
JOC2023_HAL.pdf (817.04 Ko) Télécharger le fichier
Origin Files produced by the author(s)
Licence

Dates and versions

hal-04178887 , version 1 (08-08-2023)

Licence

Identifiers

Cite

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⟩
91 View
24 Download

Altmetric

Share

Gmail Mastodon Facebook X LinkedIn More