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Synthesis of Eight-Membered Lactones: Intermolecular [6+2] Cyclization of Amphoteric Molecules with Siloxy Alkynes†

Authors

  • Wanxiang Zhao,

    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong (China)
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  • Zhaobin Wang,

    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong (China)
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  • Prof. Dr. Jianwei Sun

    Corresponding author
    1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong (China)
    • Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong (China)
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  • †

    Financial support was provided by the HKUST and NSFC (21102024). We thank Profs. H. Yamamoto, S. A. Kozmin (UChicago), L. Zhang (UCSB), and Dr. S. Lou (BMS) for helpful discussions. We also thank H. H. Sung and Prof. I. Williams for assistance in structure determination by X-ray.

Abstract

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That's about the size of it: The title molecules react with siloxy alkynes in the presence of a Brønsted acid to deliver medium-sized lactones through a [6+2] cyclization (see scheme; TIPS=triisopropylsilyl). This process is the first intermolecular synthesis of such lactones and involves a sequence of several selective ring-opening/ring-closing events.

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Article Information

DOI

10.1002/anie.201200513

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Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • alkynes;
  • cyclization;
  • homogeneous catalysis;
  • lactones;
  • medium-ring compounds

Publication History

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  • Manuscript Revised:
  • Manuscript Received:

Funded by

  • HKUST
  • NSFC. Grant Number: 21102024

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