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Sulfinyl-directed diastereoselective

Lopez1, Castedo, Mascarenas

  • 1Departamento de Quimica Organica, Universidad de Santiago de Compostela, Spain.

Organic Letters
|April 18, 2000
PubMed
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Introducing a chiral sulfinyl group accelerates cycloaddition reactions, yielding optically active intermediates. These intermediates can be used to synthesize complex natural products with high enantiomeric purity.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Thermal [5C + 2C] intramolecular cycloaddition reactions are crucial for constructing complex molecular architectures.
  • Achieving high diastereoselectivity in these reactions remains a significant challenge in synthetic chemistry.

Purpose of the Study:

  • To investigate the effect of a homochiral p-tolylsulfinyl group on the stereochemical outcome of [5C + 2C] intramolecular cycloadditions.
  • To develop a method for accessing enantiomerically pure 8-oxabicyclic[3.2.1]octane intermediates.

Main Methods:

  • The study involved the synthesis of alkenes functionalized with a homochiral p-tolylsulfinyl group.
  • Thermal [5C + 2C] intramolecular cycloaddition reactions with beta-silyloxy-gamma-pyrones were performed.
  • Desulfinylation of the resulting adducts was carried out to yield the target intermediates.

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Main Results:

  • The presence of the homochiral p-tolylsulfinyl group significantly accelerated the cycloaddition reaction.
  • Excellent levels of diastereodifferentiation were achieved in the cycloaddition step.
  • Optically active 8-oxabicyclic[3.2.1]octane intermediates were successfully synthesized via desulfinylation.

Conclusions:

  • The homochiral p-tolylsulfinyl group serves as an effective chiral auxiliary for diastereoselective [5C + 2C] intramolecular cycloadditions.
  • The synthesized intermediates are versatile building blocks for the enantioselective synthesis of natural products containing seven-membered carbocycles and tetrahydrofurans.