Synthesis and development of C3 symmetric tridentate olefin ligands
(2025) KEML10 20251Department of Chemistry
- Abstract
- Chiral C3-symmetric molecules are an important class of compounds with applications in asymmetric catalysis and drug discovery. Few synthetic methods exist to synthesize this class of molecules in a step-economic and concise manner. This work explores a range of chemical transformations to functionalize the D3-symmetric (a,e,i)tribenzo(5,6,11,12,17,18) hexadehydro[12]annulene into C3-symmetric planar chiral derivatives, which are both conceptually interesting, and of value as potential ligands in asymmetric catalysis on account of their inherent chirality. Herein, we present our efforts of breaking the symmetry of this peculiar system, including new methodology to access (a,e,i)tribenzo[12]annulene in high yield via hydrosilylation and... (More)
- Chiral C3-symmetric molecules are an important class of compounds with applications in asymmetric catalysis and drug discovery. Few synthetic methods exist to synthesize this class of molecules in a step-economic and concise manner. This work explores a range of chemical transformations to functionalize the D3-symmetric (a,e,i)tribenzo(5,6,11,12,17,18) hexadehydro[12]annulene into C3-symmetric planar chiral derivatives, which are both conceptually interesting, and of value as potential ligands in asymmetric catalysis on account of their inherent chirality. Herein, we present our efforts of breaking the symmetry of this peculiar system, including new methodology to access (a,e,i)tribenzo[12]annulene in high yield via hydrosilylation and subsequent alcoholysis and protodesilylation. We also present the preparation of an enantiopure cross-coupling partner, which holds the potential to enable a great variety of compounds in this elusive class of C3-symmetric chiral olefins. (Less)
- Popular Abstract
- Chirality is an important aspect of life, as the building blocks for every protein in our body, the amino acids, are chiral. A chemical being chiral means that its mirror images are not identical, much like our own hands. No matter how much you try, you cannot perfectly overlay one over the other. These mirror images are known as enantiomers.
Due to the innate chirality of our bodies, it is of no surprise that pharmaceuticals also depend heavily on this property. Enantiomers have identical physical properties, such as their melting points and density, but they may differ within biological systems. In a lot of cases, one enantiomer may be highly active, while the other has low to no activity. In some cases however, one enantiomer may be... (More) - Chirality is an important aspect of life, as the building blocks for every protein in our body, the amino acids, are chiral. A chemical being chiral means that its mirror images are not identical, much like our own hands. No matter how much you try, you cannot perfectly overlay one over the other. These mirror images are known as enantiomers.
Due to the innate chirality of our bodies, it is of no surprise that pharmaceuticals also depend heavily on this property. Enantiomers have identical physical properties, such as their melting points and density, but they may differ within biological systems. In a lot of cases, one enantiomer may be highly active, while the other has low to no activity. In some cases however, one enantiomer may be detrimental. This was infamously the case with thalidomide, in which one enantiomer gave the desired effect of the suppression of morning illness, while the other enantiomer was teratogenic, meaning it harmed unborn children. Due to this, drugs are often sold as pure enantiomers.
Chirality is however not only present in the drug molecule, but is also routinely found in the catalysts used during the synthesis thereof. These chiral catalysts are typically metal complexes, which are compounds where a molecule, known as a ligand, is bound to a metal atom.
Commonly, these ligands are symmetric, and are identical if rotated 180o, which is known as twofold rotational symmetry, or C2-symmetry. More rarely, ligands with threefold rotational symmetry, C3-symmetry, are seen, but these can offer unique advantages over C2-symmetry in some processes. Herein, we present our efforts towards the synthesis of a new class of C3-symmetric molecules, with potential applications for the synthesis of chiral molecules. (Less)
Please use this url to cite or link to this publication:
http://lup.lub.lu.se/student-papers/record/9208047
- author
- Nyberg, Vilhelm LU
- supervisor
- organization
- course
- KEML10 20251
- year
- 2025
- type
- M2 - Bachelor Degree
- subject
- keywords
- organic chemistry, C3 symmetry, hydrosilylation, protodesilylation, symmetric addition, symmetric substitution
- language
- English
- id
- 9208047
- date added to LUP
- 2025-07-07 10:01:57
- date last changed
- 2025-07-07 10:01:57
@misc{9208047,
abstract = {{Chiral C3-symmetric molecules are an important class of compounds with applications in asymmetric catalysis and drug discovery. Few synthetic methods exist to synthesize this class of molecules in a step-economic and concise manner. This work explores a range of chemical transformations to functionalize the D3-symmetric (a,e,i)tribenzo(5,6,11,12,17,18) hexadehydro[12]annulene into C3-symmetric planar chiral derivatives, which are both conceptually interesting, and of value as potential ligands in asymmetric catalysis on account of their inherent chirality. Herein, we present our efforts of breaking the symmetry of this peculiar system, including new methodology to access (a,e,i)tribenzo[12]annulene in high yield via hydrosilylation and subsequent alcoholysis and protodesilylation. We also present the preparation of an enantiopure cross-coupling partner, which holds the potential to enable a great variety of compounds in this elusive class of C3-symmetric chiral olefins.}},
author = {{Nyberg, Vilhelm}},
language = {{eng}},
note = {{Student Paper}},
title = {{Synthesis and development of C3 symmetric tridentate olefin ligands}},
year = {{2025}},
}