Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Bifunctional Quaternary Ammonium Salts Catalyzed Stereoselective Conjugate Addition of Oxindoles to Electron-Deficient β-Haloalkenes

Bifunctional Quaternary Ammonium Salts Catalyzed Stereoselective Conjugate Addition of Oxindoles to Electron-Deficient β-Haloalkenes
Qiaowen Jin, Gang Zou, Changwu Zheng, Gang Zhao
A highly Z-selective asymmetric conjugate addition of 3-substituted oxindoles to β-haloalkene ketones/esters catalyzed by readily available chiral bifunctional quaternary ammonium salts is reported. This reaction provides efficient access to a range of 2-oxoindole derivatives bearing a thermodynamically unstable Z-olefin structure and a chiral quaternary carbon center in high yields (up to 90%) and with good to high stereoselectivities (up to >19:1 Z/E and 91% ee) under mild conditions.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00571

DOI: 10.1021/acs.joc.7b00571

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.