5 years ago

Substrate-Triggered Stereoselective Preparation of Highly Substituted Organic Carbonates

Substrate-Triggered Stereoselective Preparation of Highly Substituted Organic Carbonates
Eddy Martin, Victor Laserna, Eduardo C. Escudero-Adán, Arjan W. Kleij
Trisubstituted cyclic organic carbonates with multiple though well-defined stereochemical configurations are difficult to prepare. Here we present a conceptual design toward these CO2-based synthons using hydroxyl-substituted cyclic epoxide precursors and their catalytic conversion, to afford these challenging target compounds with fused ring sizes of up to eight under excellent stereocontrol. The observed stereochemistry of the organic carbonates combined with various control experiments revealed that these compounds are formed through a mechanistic manifold that involves a depolymerization reaction within an oligomeric carbonate induced by a pendant hydroxyl nucleophile. This manifold therefore provides an alternative approach toward CO2 valorization into functional cyclic carbonate scaffolds of use in synthetic chemistry.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b01748

DOI: 10.1021/acscatal.7b01748

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.