Gold-Catalyzed Addition of Propargyl Acetates to Olefins via O -Acyl Migration/Cyclopropanation Sequence: Insight into the Diastereoselective Formation of the Alkene - Chimie Structurale Organique et Biologique 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.
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hal-04178887 , version 1 (08-08-2023)

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Attribution - NonCommercial - NoDerivatives

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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⟩
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