Iridium‐Catalyzed Stereoselective Allylic Alkylation Reactions with Crotyl Chloride

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  • J. Caleb Hethcox
    The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101-20 Pasadena CA 91125 USA
  • Samantha E. Shockley
    The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101-20 Pasadena CA 91125 USA
  • Brian M. Stoltz
    The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering California Institute of Technology 1200 E. California Blvd, MC 101-20 Pasadena CA 91125 USA

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<jats:title>Abstract</jats:title><jats:p>The development of the first enantio‐, diastereo‐, and regioselective iridium‐catalyzed allylic alkylation reaction of prochiral enolates to form an all‐carbon quaternary stereogenic center with an aliphatic‐substituted allylic electrophile is disclosed. The reaction proceeds with good to excellent selectivity with a range of substituted tetralone‐derived nucleophiles furnishing products bearing a newly formed vicinal tertiary and all‐carbon quaternary stereodyad. The utility of this protocol is further demonstrated via a number of synthetically diverse product transformations.</jats:p>

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