Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

(E)- and (Z)-Stereodefined Enol Sulfate Esters Derived from α-Aryl Aldehydes: Stereocomplementary Synthesis of Styryl Sulfate Natural Products

(E)- and (Z)-Stereodefined Enol Sulfate Esters Derived from α-Aryl Aldehydes: Stereocomplementary Synthesis of Styryl Sulfate Natural Products
Feng Li, Shuai Yu, Sanghee Kim
A method for the stereoselective formation of enol sulfate esters from α-aryl aldehydes is described. This method involved the stereocontrolled enolization of a carbonyl group with DBU or t-BuOK followed by trapping with a reactive sulfuryl imidazolium salt, providing the corresponding styryl enol sulfate esters in good to excellent yields and stereoselectivities. This method was applied to the first total synthesis of the enol sulfate natural products in a stereocomplementary manner.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00868

DOI: 10.1021/acs.joc.7b00868

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.