Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Gold(I)-Catalyzed Cycloisomerization–Dimerization Cascade of Benzene-Tethered 1,6-Enynes

Gold(I)-Catalyzed Cycloisomerization–Dimerization Cascade of Benzene-Tethered 1,6-Enynes
María C. de la Torre, María Frutos, Catherine Hemmert, Heinz Gornitzka, Alma Viso, Mónica Álvarez-Pérez, Roberto Fernández de la Pradilla, Miguel A. Sierra
An unprecedented stereoselective domino reaction of 1,6-enynes with an aryl ring at C3–C4 in the presence of gold(I) catalysts at low temperature is described. This process involves a novel 5-exo-dig cycloisomerization–dimerization sequence to afford formal Diels–Alder adducts that undergo a smooth gold-catalyzed double bond migration at room temperature. In addition, the first examples of the gold mesoionic carbene mediated [2+2+2] cycloaddition of these enynes with benzaldehyde are reported.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01273

DOI: 10.1021/acs.joc.7b01273

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.