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Generation of Organolithium Compounds bearing Super Silyl Ester and their Application to Matteson Rearrangement

Authors

  • Susumu Oda,

    1. Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637 (USA)
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  • Prof. Dr. Hisashi Yamamoto

    Corresponding author
    1. Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637 (USA)
    2. Molecular Catalyst, Research Center, Chubu University, 1200 Matsumoto, Kasugai, Aichi 487-8501 (Japan)
    • Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637 (USA)
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  • This work was supported by the NIH (P50GM086145-01). We would like to thank Dr. Antoni Jurkiewicz and Dr. Jin Qin for their expertise in NMR spectroscopy and mass spectrometry, respectively.

Abstract

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It's super-silyl-fragilithyl-ester-aryl-docious: The super silyl group is a strong protecting group for carboxylic acids and provides a method for direct lithiation that is compatible with the ester moiety. Organolithium compounds bearing a super silyl ester react with a variety of electrophiles in high yields (see scheme). The reaction of lithiated super silyl chloroacetate with a boron compound gives α-functionalization of the ester moiety by Matteson rearrangement.

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