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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.
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