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Synthesis

Metathesis Method for Z Allylic Alcohols

Ruthenium disulfide catalyst creates high-value compounds via cross-metathesis

by Bethany Halford
January 12, 2015 | A version of this story appeared in Volume 93, Issue 2

Making acyclic Z allylic alcohols—a useful but tough-to-synthesize molecular motif—just got easier thanks to a new ruthenium disulfide catalyst. Chemists at Boston College led by Amir H. Hoveyda created the catalyst from a commercially available precursor and an easily generated air-stable zinc catechothiolate. This catalyst turns out to be ideal for spurring on Z-selective cross-metathesis reactions of (Z)-2-butene-1,4-diol and other alkenes to generate acyclic Z allylic alcohols (Nature 2015, DOI: 10.1038/nature14061). During the cross-metathesis transformation, two carbon-carbon double bonds react in such a way that they switch bonding partners. By using (Z)-2-butene-1,4-diol as one of the metathesis partners, Hoveyda’s group was able to create a variety of Z allylic alcohols, including examples containing aldehydes, carboxylic acids, and bulky neighboring groups. In one instance (shown), the chemists used oleic acid as the second metathesis partner, creating in one fell swoop an antifungal agent with an allylic alcohol and a second allylic alcohol that could be used as a substrate for stereoselective organic synthesis.

Reaction scheme shows how to make acyclic Z allylic alcohols using a ruthenium disulfide catalyst.

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