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Related Experiment Videos

Stereoselectivity and regioselectivity in the segment-coupling Prins cyclization.

J J Jaber1, K Mitsui, S D Rychnovsky

  • 1Department of Chemistry, University of California, Irvine, CA 92697-2025, USA.

The Journal of Organic Chemistry
|June 26, 2001
PubMed
Summary

This study explores segment-coupling Prins cyclizations for synthesizing tetrahydropyrans. Alkene geometry controls stereochemistry, offering a versatile method for organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Stereoselective Synthesis

Background:

  • The Prins cyclization is a valuable reaction in organic synthesis.
  • Controlling stereochemistry in cyclization reactions is crucial for creating complex molecules.

Purpose of the Study:

  • To investigate the scope and limitations of the segment-coupling Prins cyclization.
  • To establish the stereoselectivity and regioselectivity of this reaction for tetrahydropyran synthesis.

Main Methods:

  • Esterification of homoallylic alcohols followed by reductive acetylation.
  • Lewis acid-catalyzed cyclization of alpha-acetoxy ethers.
  • Investigation of various dienols and alkene geometries.

Main Results:

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  • Alkene geometry (E vs. Z) dictates product stereochemistry (equatorial vs. axial substituents).
  • Dienols with one allylic and one homoallylic alkene cyclize efficiently.
  • Dienols with two homoallylic alkenes show modest to high regioselectivity.
  • Relative cyclization rates established: vinyl > Z-alkene > E-alkene > alkyne.

Conclusions:

  • The segment-coupling Prins cyclization provides a stereoselective and regioselective route to tetrahydropyrans.
  • Product configurations are consistent with cyclization through a chair conformation.
  • The 2-oxonia Cope rearrangement may influence regioselectivity and stereoselectivity in diene cyclizations.