ADVERTISEMENT
2 /3 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

Metathesis Method for Z Allylic Alcohols

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

by Bethany Halford
January 12, 2015 | 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.

X

Article:

This article has been sent to the following recipient:

Leave A Comment

*Required to comment