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Asymmetric Epoxidation Reaction Using MIB

By: William Sommer, Aldrich ChemFiles 2008, 8.6, 12.

Aldrich ChemFiles 2008, 8.6, 12.

Chiral epoxy alcohols are essential building blocks extensively used in the synthesis of natural products. However, the synthesis of these molecules proved to be challenging, especially allylic alcohols containing (E)-olefins. To access a plethora of chiral epoxy alcohols Professor Walsh and coworkers have invented a novel methodology,1,2 which complements the Sharpless asymmetric epoxidation. This process is mediated by a zinc catalyst built around Nugent’s (–)-MIB ligand. Starting with a substituted terminal alkyne, the one pot reaction yields the desired epoxy alcohols with excellent levels of enantiocontrol, as well as yielding moderate to excellent diastereomeric ratios for a wide array of substrates.


Scheme 1.

Materials

     

References

  1. Jeon, S. -J. et al. Org. Lett. 2005, 7, 1729.
  2. Lurain, A. E. et al. J. Org. Chem. 2005, 70, 1262.

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