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Domino Carbopalladation-Carbonylation: Investigation of Substrate Scope

Authors

  • Brinton Seashore-Ludlow,

    1. Organic Chemistry, Chemical Science and Engineering, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden, Fax: (+46)-8-791-2233
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  • Jakob Danielsson,

    1. Organic Chemistry, Chemical Science and Engineering, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden, Fax: (+46)-8-791-2233
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  • Peter Somfai

    Corresponding author
    1. Organic Chemistry, Chemical Science and Engineering, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden, Fax: (+46)-8-791-2233
    2. Section for Organic Chemistry, Institute of Technology, University of Tartu, 50411 Tartu, Estonia
    • Organic Chemistry, Chemical Science and Engineering, KTH Royal Institute of Technology, 100 44 Stockholm, Sweden, Fax: (+46)-8-791-2233
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Abstract

This work gives an in depth account of our domino carbopalladation-carbonylation method for substrates possessing β-hydrogens. The scope of the method is examined for allylic amines containing trisubstituted olefins and we detail our attempts toward the diastereospecific synthesis of contiguous quaternary centers using this technology. The results give key insights into the relative rates of the competing reactions of the alkyl palladium intermediates, which is crucial for the understanding and development of new domino processes.

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