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Gold-catalyzed stereocontrolled synthesis of 2,3-bis(acetoxy)-1,3-dienes


Huang, X; De Haro, T; Nevado, C (2009). Gold-catalyzed stereocontrolled synthesis of 2,3-bis(acetoxy)-1,3-dienes. Chemistry - A European Journal, 15(24):5904-5908.

Abstract

Change the ligand, change the stereochemistry: 2,3-Bis(acetoxy)-1,3-dienes are obtained in a stereocontrolled manner by a novel tandem 1,2-/1,2-bis(acetoxy) rearrangement (see scheme, R1 and R2 are + stabilizing). Upon stabilization of the reaction intermediates, the ligand attached to gold controls the stereochemistry of the alkene in the second acetate migration, that is, N-heterocyclic carbenes (NHC) favor cis alkenes, whereas phosphine ligands selectively afford trans olefins.

Change the ligand, change the stereochemistry: 2,3-Bis(acetoxy)-1,3-dienes are obtained in a stereocontrolled manner by a novel tandem 1,2-/1,2-bis(acetoxy) rearrangement (see scheme, R1 and R2 are + stabilizing). Upon stabilization of the reaction intermediates, the ligand attached to gold controls the stereochemistry of the alkene in the second acetate migration, that is, N-heterocyclic carbenes (NHC) favor cis alkenes, whereas phosphine ligands selectively afford trans olefins.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2009
Deposited On:15 Jan 2010 10:22
Last Modified:05 Apr 2016 13:37
Publisher:Wiley-Blackwell
ISSN:0947-6539
Publisher DOI:https://doi.org/10.1002/chem.200900391
Permanent URL: https://doi.org/10.5167/uzh-25335

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