Synthesis of a Molecular Tweezer Based on Norbornadiene Framework: Unexpected Stereoselectivity

Cücü E., EŞSİZ S., ŞAHİN E., Dalkılıç E.

Asian Journal of Organic Chemistry, vol.14, no.6, 2025 (Scopus) identifier

  • Publication Type: Article / Article
  • Volume: 14 Issue: 6
  • Publication Date: 2025
  • Doi Number: 10.1002/ajoc.202500152
  • Journal Name: Asian Journal of Organic Chemistry
  • Journal Indexes: Scopus
  • Keywords: DFT calculations, Imine condensation, Molecular tweezer, Stereoselectivity
  • Hakkari University Affiliated: Yes

Abstract

In this study, a new type of Klarner tweezer, which has multiple hydrogen bonding acceptors, was synthesized. This tweezer is based on the bicyclo[2.2.1]heptane framework and comprises two near-parallel flat aromatic rings as pincers and a pyrazine unit as the tether. The synthesis was carried out by the annulation of a bicyclic α-amino ketone. Surprisingly, this reaction took place stereo-selectively, though the initial alpha-amino ketone starting material was racemic. This unexpected result was explained by theoretical studies.