Palladium(0)-catalyzed allylic alkylation of diketoester-dioxinones with allyl acetates under neutral conditions: synthesis of hexasubstituted benzene derivatives

Jens Cordes; Sylvain Laclef; Andrew J P White; Anthony G M Barrett

doi:10.1021/jo300340c

Palladium(0)-catalyzed allylic alkylation of diketoester-dioxinones with allyl acetates under neutral conditions: synthesis of hexasubstituted benzene derivatives

J Org Chem. 2012 Apr 6;77(7):3524-30. doi: 10.1021/jo300340c. Epub 2012 Mar 27.

Authors

Jens Cordes¹, Sylvain Laclef, Andrew J P White, Anthony G M Barrett

Affiliation

¹ Department of Chemistry, Imperial College, London SW7 2AZ, England.

PMID: 22420647
DOI: 10.1021/jo300340c

Abstract

Intermolecular palladium(0)-catalyzed allylic alkylation of diketoester-dioxinones was performed under neutral conditions with 2-alkenyl and 2-cycloalkenyl acetates. Subsequent aromatization using cesium carbonate gave rise to isopropylidene-protected hexasubstituted resorcylates.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Allyl Compounds / chemistry*
Benzene Derivatives / chemical synthesis*
Benzene Derivatives / chemistry
Carboxylic Acids / chemistry*
Catalysis
Molecular Structure
Palladium / chemistry*

Substances

Allyl Compounds
Benzene Derivatives
Carboxylic Acids
Palladium