Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Enantioselective Synthesis of Functionalized β-Lactones by NHC-Catalyzed Aldol Lactonization of Ketoacids

Enantioselective Synthesis of Functionalized β-Lactones by NHC-Catalyzed Aldol Lactonization of Ketoacids
Santigopal Mondal, Tamal Kanti Das, Akkattu T. Biju, Rajesh G. Gonnade, Subrata Mukherjee
N-Heterocyclic carbene (NHC)-catalyzed intramolecular aldol lactonization of readily available ketoacids leading to the enantioselective synthesis of cyclopentane-fused β-lactones is presented. The reaction proceeds via the generation of NHC-bound enolate intermediates formed from the ketoacids in the presence of the peptide coupling reagent HATU and NHC generated from the chiral triazolium salt. The functionalized β-lactones are formed under mild conditions in high yields and enantioselectivities.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01526

DOI: 10.1021/acs.joc.7b01526

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.