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

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 alpha-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.

Dergi

ASIAN JOURNAL OF ORGANIC CHEMISTRY

Yıl

2025

Cilt

14

Sayı

6

ISSN

2193-5807

eISSN

2193-5815

DOI

10.1002/ajoc.202500152

WoS UID

WOS:001461337200001