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A general model for selectivity in olefin cross metathesis.

Arnab K Chatterjee1, Tae-Lim Choi, Daniel P Sanders

  • 1Arnold and Mabel Beckman Laboratories for Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.

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A new model predicts selectivity in olefin cross metathesis (CM). This advances organic synthesis by enabling precise control over reactions involving diverse olefins and catalysts.

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Area of Science:

  • Organic Chemistry
  • Synthetic Methodology
  • Catalysis

Background:

  • Olefin cross metathesis (CM) is a valuable synthetic tool.
  • Predicting product selectivity and stereoselectivity in CM remains a challenge.
  • Existing CM methods lack general predictability for diverse olefin classes.

Purpose of the Study:

  • To develop a general model for predicting selectivity in olefin cross metathesis.
  • To enable predictable stereoselective and regioselective CM reactions.
  • To expand the scope of CM to include challenging substrates.

Main Methods:

  • Investigated cross metathesis with various olefins: styrenes, allylic alcohols, and alpha-quaternary olefins.
  • Developed a reactivity ranking based on homodimerization and secondary metathesis susceptibility.
  • Employed metathesis catalysts with varying activity to control selectivity.

Main Results:

  • Established a general model for predicting product selectivity and stereoselectivity in CM.
  • Demonstrated selective CM using a 1:1 stoichiometry of high-reactivity and low-reactivity olefins.
  • Achieved selective cross metathesis with electron-rich, electron-deficient, and sterically hindered olefins.
  • Successfully applied the model to develop unprecedented three-component intermolecular CM reactions.

Conclusions:

  • The developed model provides a predictive framework for olefin cross metathesis selectivity.
  • This work significantly enhances the utility and predictability of CM in organic synthesis.
  • The findings pave the way for designing complex molecules through selective CM strategies.