Organic Letters
Organic Letters
5 years ago

β-Silyl-Assisted Tandem Diels–Alder/Nazarov Reaction of 1-Aryl-3-(trimethylsilyl) Ynones

β-Silyl-Assisted Tandem Diels–Alder/Nazarov Reaction of 1-Aryl-3-(trimethylsilyl) Ynones
Wesley A. Chalifoux, Punyanuch Sophanpanichkul, Rachael A. Carmichael
A one-pot tandem Diels–Alder/Nazarov reaction of 1-aryl-3-(trimethylsilyl) ynones has been achieved to generate carbo- and heterocyclic fused ring systems in good to excellent yields. The β-silyl effect is instrumental in accessing this otherwise challenging cascade annulation reaction. The tandem reaction proceeds in the presence of BCl3 to generate three new carbon–carbon bonds, a quaternary carbon, and two stereogenic centers with excellent diastereocontrol. A variety of substituted arenes, and even heteroaromatics, are tolerated to provide tricyclic products that are of interest as advanced intermediates toward biologically relevant compounds.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00911

DOI: 10.1021/acs.orglett.7b00911

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.