Asymmetric Syntheses of 8-Oxabicyclo[3,2,1]octanes: A Cationic Cascade Cyclization

Authors

  • Bin Li,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore)
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  • Dr. Yu-Jun Zhao,

    1. Departments of Internal Medicine, University of Michigan, Ann Arbor, MI 48109 (USA)
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  • Yin-Chang Lai,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore)
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  • Prof. Teck-Peng Loh

    Corresponding author
    1. Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)
    2. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore)
    • Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)
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  • We gratefully acknowledge the Nanyang Technological University, the Singapore Ministry of Education Academic Research Fund Tier 2 (MOE2010- T2-2-067), and Tier 2 MOE2011-T2-1-013 for financial support.

Abstract

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High octane: A novel and practical syntheses of 8-oxabicyclo[3.2.1]octanes using a cationic cascade cyclization reaction has been developed (see scheme; TIPS=triisopropylsilyl). The diastereomer of the cyclization product isolated depends upon whether the acetal or aldehyde substrate is used.

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