Twisted amide analogues of Tröger's base

Josep Artacho, Erhad Ascic, Toni Rantanen, Josefine Karlsson, Carl Johan Wallentin, Ruiyao Wang, Ola F. Wendt, Michael Harmata, Victor Snieckus, Kenneth Wärnmark*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

Let's do the twist: The first twisted bis-amide (see figure) is obtained by the benzylic oxidation of Tröger's base (TB). Kinetic studies of its acidic hydrolysis reveal that the hydrolysis is to a large extent funneled through doubly protonated species.

Original languageEnglish
Pages (from-to)1038-1042
Number of pages5
JournalChemistry - A European Journal
Volume18
Issue number4
DOIs
Publication statusPublished - 23 Jan 2012
Externally publishedYes

Keywords

  • Tröger's base
  • X-ray structures
  • hydrolysis
  • oxidation
  • twisted amides

Cite this

Artacho, J., Ascic, E., Rantanen, T., Karlsson, J., Wallentin, C. J., Wang, R., Wendt, O. F., Harmata, M., Snieckus, V., & Wärnmark, K. (2012). Twisted amide analogues of Tröger's base. Chemistry - A European Journal, 18(4), 1038-1042. https://doi.org/10.1002/chem.201103228