3 years ago

Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994

Synthesis of Enantiopure Mixed Alkyl-Aryl Vicinal Diamines by the Diaza-Cope Rearrangement: A Synthesis of (+)-CP-99,994
Jik Chin, Hyunwoo Kim, Hyeseung Kim, Miji Kim
The stereoselective synthesis of mixed alkyl-aryl vicinal diamines was demonstrated by the use of 1,2-bis(2-hydroxyphenyl)-1,2-diaminoethene (hpen). A sequential addition of aryl and alkyl aldehyde to hpen gave a fused imidazolidine-dihydro-1,3-oxazine ring stereoselectively, which undergoes the diaza-Cope rearrangement to provide mixed vicinal diimines at elevated temperature in good yields and excellent stereoselectivity. We also showed that (+)-CP-99,994 can be readily prepared by the diaza-Cope rearrangement in overall 42% yield.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01751

DOI: 10.1021/acs.joc.7b01751

You might also like
Never Miss Important Research

Researcher is an app designed by academics, for academics. Create a personalised feed in two minutes.
Choose from over 15,000 academics journals covering ten research areas then let Researcher deliver you papers tailored to your interests each day.

  • 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.