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Related Experiment Videos

Kinetically controlled cross-metathesis reactions with high E-olefin selectivities.

F C Engelhardt1, M J Schmitt, R E Taylor

  • 1Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, Indiana 46556-5670, USA.

Organic Letters
|July 7, 2001
PubMed
Summary

Homoallylic alcohols with anti-allylic substituents improve E-olefin selectivity in cross-metathesis reactions. A five-membered chelate intermediate involving the hydroxyl group and ruthenium catalyst explains this enhanced selectivity.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Stereoselective Synthesis

Background:

  • Cross-metathesis (CM) is a powerful tool for C=C bond formation.
  • Controlling stereoselectivity, particularly E-olefin formation, remains a key challenge in CM reactions.

Purpose of the Study:

  • To investigate factors influencing E-olefin selectivity in CM reactions.
  • To explore the role of substituents on homoallylic alcohols in dictating CM outcomes.

Main Methods:

  • Cross-metathesis reactions using various homoallylic alcohols and allyltrimethylsilane.
  • Ruthenium-catalyzed reactions employing Grubbs' catalyst.
  • Analysis of reaction products to determine E/Z selectivity.

Main Results:

Related Experiment Videos

  • Homoallylic alcohols bearing anti-allylic substituents demonstrated significantly enhanced E-olefin selectivity.
  • The presence of specific substituents promoted higher yields of the desired E-isomer.

Conclusions:

  • Anti-allylic substituents on homoallylic alcohols are crucial for achieving high E-olefin selectivity in CM.
  • A proposed five-membered chelate intermediate, involving hydroxyl-ruthenium coordination, explains the observed stereochemical preference.