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Related Experiment Videos

Indium trichloride mediated intramolecular Prins-type cyclization.

Yong Seo Cho1, Hye Yeon Kim, Joo Hwan Cha

  • 1Biochemicals Research Center, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea. ys4049@kist.re.kr

Organic Letters
|June 7, 2002
PubMed
Summary

This study details intramolecular Prins-type reactions using indium trichloride, successfully synthesizing bicyclic compounds like 9-oxabicyclo[3.3.1]nonane and 3,9-dioxabicyclo[3.3.1]nonane. These reactions offer a new pathway for creating complex molecular structures.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Prins cyclization is a valuable reaction for forming cyclic ethers.
  • Intramolecular reactions offer enhanced selectivity and efficiency.

Purpose of the Study:

  • To explore intramolecular Prins-type reactions of homoallyl alcohol and acetal moieties.
  • To develop efficient synthetic routes to bicyclic ethers.

Main Methods:

  • Reactions were catalyzed by indium trichloride.
  • Solvents included chloroform and 25% aqueous tetrahydrofuran (THF).

Main Results:

  • Successful synthesis of 9-oxabicyclo[3.3.1]nonane derivatives.
  • Successful synthesis of 3,9-dioxabicyclo[3.3.1]nonane derivatives.

Related Experiment Videos

  • Moderate yields were achieved for both product types.

    • Conclusions:

    • Indium trichloride effectively promotes intramolecular Prins-type cyclizations.
    • This method provides a viable route to complex bicyclic ether scaffolds.