A Regioselective Palladium-Catalyzed Reduction of 3,3-Heterobimetalated Allylic Acetates— Synthesis and Reactivity of Allylic Bimetallic Compounds

Authors

  • Prof. Mark Lautens,

    Corresponding author
    1. Department of Chemistry, University of Toronto Toronto, Ontario M5S 1A1 (Canada) Telefax: Int. code + (416)978-6083
    • Department of Chemistry, University of Toronto Toronto, Ontario M5S 1A1 (Canada) Telefax: Int. code + (416)978-6083
    Search for more papers by this author
  • Patrick H. M. Delanghe

    1. Department of Chemistry, University of Toronto Toronto, Ontario M5S 1A1 (Canada) Telefax: Int. code + (416)978-6083
    Search for more papers by this author

  • This research was supported by the following fellowships: E. W. R. Steacie Fellow, Alfred P. Sloan Foundation Fellow, NSERC (Canada) University Research Fellow, Bio-Mega Young Investigator, Eli Lilly Grantee. P. H. M. D. thanks the Province of Ontario for an Ontario Graduate Scholarship and the University of Toronto for a Simcoe Scholarship.

Abstract

original image

Selective reaction of one of two C[BOND]Si bonds in 1 with octanal yields 2. The disilyl compound 1 and also silylstannyl compounds, useful reagents in organic synthesis, could be prepared regioselectively (>99:1) by hydride reduction of allylic acetates.

Ancillary