An N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirooxindole Lactones

Authors

  • Dr. Julien Dugal-Tessier,

    1. Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA)
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  • Dr. Elizabeth A. O'Bryan,

    1. Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA)
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  • Thomas B. H. Schroeder,

    1. Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA)
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  • Daniel T. Cohen,

    1. Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA)
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  • Prof. Karl A. Scheidt

    Corresponding author
    1. Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA)
    • Department of Chemistry, Center for Molecular Innovation and Drug Discovery, Chemistry of Life Processes Institute, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208 (USA)
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  • Financial support has been generously provided by the NIH (NIGMS RO1-GM073072). T.B.H.S. was supported by a 2011 Northwestern Summer Undergraduate Research Grant. D.T.C thanks the ACS Division of Organic Chemistry for a 2011-12 Graduate Fellowship (sponsored by Organic Synthesis/Organic Reactions). We thank Michael Katz (NU) and John M. Roberts (NU) for assistance with X-ray crystallography.

Abstract

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Durch kooperative Katalyse gelingt die enantioselektive formale [3+2]-Addition von α,β-ungesättigten Aldehyden an Isatine. Diese Homoenolatcyclisierungen von β-Arylenalen mit einem N-heterocyclischen Carben (NHC) als Katalysator ergeben erst bei Zusatz von Lithiumchlorid hohe Enantioselektivitäten. Als Anwendungsbeispiel wird die Totalsynthese von Maremycin B vorgestellt.

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