Nitrogen containing heterocyclic compounds (the most widely known are bipyridine and phenanthroline types) act as ligands in coordination with palladium, copper, molybdenum etc. There is a possibility to prepare compounds which are suitable for enantioselective catalysis by implementation of chiral centre to these systems. It seems to be very convenient using of natural raw materials as carriers of chirality [1]. Model of 2-fenylimidazole as a nitrogen containing heterocycle has been chosen. Pinocarvone has been used as the source of chirality. 9,9-Dimethyl-4-phenyl-3,5- diazatricyclo[6.1.1.0^2,6]deca-2(6),4-diene has become final molecule in this case.

The synthesis has been done by condensation of benzaldehyde with PinDione [2] and ammonium acetate in propan-2-ole. The derivate synthesized has been characterized by the GC/MS, ¹H and ¹³C NMR spectra and elemental analysis. Optical rotation alfa_D²⁰ = -21° (methanol, c = 0,4) has been obtained. The synthesized derivate has been used as a ligand for complexation with copper chloride. Benzene ring could be also replaced by 2-pyridyle ring to improve complexation ability.

[1] G. Chelucci, G. Loriga, G. Murineddu, G. A. Pinna, Synthesis 2003, 73-78.

[2] Ch. Michno, J.-P. Djukic, Z. Ratkovic, M. Pfeffer, Tetrahedron Lett. 2002, 43, 5241-5243.

The authors are indebted to the Ministry of Education, Youth and Sports of the Czech Republic for financial support (Research project MSM 0021627501).

• Legal notice:
  

  Copyright (c) Pielaszek Research, all rights reserved.
  The above materials, including auxiliary resources, are subject to Publisher's copyright and the Author(s) intellectual rights. Without limiting Author(s) rights under respective Copyright Transfer Agreement, no part of the above documents may be reproduced without the express written permission of Pielaszek Research, the Publisher. Express permission from the Author(s) is required to use the above materials for academic purposes, such as lectures or scientific presentations.
  In every case, proper references including Author(s) name(s) and URL of this webpage: https://science24.com/paper/8257 must be provided.

1. Coordination Properties of Imidazole Derivatives