Inside Cover: Lewis Acid Activated Synthesis of Highly Substituted Cyclopentanes by the N-Heterocyclic Carbene Catalyzed Addition of Homoenolate Equivalents to Unsaturated Ketoesters (Angew. Chem. Int. Ed. 7/2011)

Authors

  • 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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  • Dr. Benoit Cardinal-David,

    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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Abstract

original image

A highly diastereo- and enantioselective N-heterocyclic carbene catalyzed/titanium(IV)-mediated homoenolate addition to β,γ-unsaturated α-ketoesters to assemble cyclopentanols with four contiguous stereogenic centers is described by Scheidt and co-workers in their Communication on page 1678 ff. The Lewis acid is essential for the reaction and a wide range of β,γ-unsaturated α-ketoesters and enals are tolerated, with the products obtained in 52–85% yield and up to 99% ee.

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