Communication

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

  1. Bin Li2,
  2. Dr. Yu-Jun Zhao3,
  3. Yin-Chang Lai2,
  4. Prof. Teck-Peng Loh1,2,*

Article first published online: 2 JUL 2012

DOI: 10.1002/anie.201202699

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 32, pages 8041–8045, August 6, 2012

Additional Information

How to Cite

Li, B., Zhao, Y.-J., Lai, Y.-C. and Loh, T.-P. (2012), Asymmetric Syntheses of 8-Oxabicyclo[3,2,1]octanes: A Cationic Cascade Cyclization. Angew. Chem. Int. Ed., 51: 8041–8045. doi: 10.1002/anie.201202699

Author Information

  1. 1

    Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)

  2. 2

    Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616 (Singapore)

  3. 3

    Departments of Internal Medicine, University of Michigan, Ann Arbor, MI 48109 (USA)

*Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026 (China)

  1. †

    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.

Publication History

  1. Issue published online: 1 AUG 2012
  2. Article first published online: 2 JUL 2012
  3. Manuscript Revised: 24 MAY 2012
  4. Manuscript Received: 7 APR 2012

Funded by

  • Nanyang Technological University
  • Singapore Ministry of Education Academic Research Fund Tier 2. Grant Numbers: MOE2010- T2-2-067, MOE2011-T2-1-013

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Keywords:

  • aldol reaction;
  • cyclization;
  • heterocycles;
  • synthetic methods;
  • titanium
Thumbnail image of graphical abstract

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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