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Chiral ligand and chiral induction
Presented by-
Sandeep Bindra
Chiral ligand-
• Chiral ligand are used in asymmetric synthesis.
• Most of the chiral ligand combine with metals to form chiral catalyst.
• Chiral catalyst engages in chemical reaction in which chirality is
transfer to the reaction product.
• If we want to create a new chiral center in a molecule, our starting
material must have prochirality(the ability to become chiral in one
simple transformation).
• The most common prochiral units that give rise to new chiral centers
are the trigonal carbon atom of alkenes and carbonyl groups, which
become tetrahedral by addition reaction.
• One of the simplest transformations you could imagine of a prochiral
unit in to a chiral one is the reduction of ketone.
• FIRST CATALYTIC SYMMETRIC SYNTHESIS- SYNTHESIS OF L-DOPA
CHIRAL INDUCTION-
It describe the formation of an excess of an enantiomer over the other
from an achiral or racemic substrate using a chiral catalyst or chiral
reagent is called chiral induction.
EXAMPLES OF HOMOGENOUS CATALYSIS USED IN SYNTHESIS OF
DRUGS-
• Synthesis of L-DOPA-
• Synthesis of (R) Naproxen-
• Synthesis of S Ibuprofen-
• Synthesis of (R) Citronellal-
References-
• Han, X., Zhang, J., Huang, J., Wu, X., Yuan, D., Liu, Y., & Cui, Y. (2018). Chiral
induction in covalent organic frameworks. Nature Communications, 9(1).
https://doi.org/10.1038/s41467-018-03689-9
• Pyarasani RD, John A, Santos LS. Recent developments of chiral induction in
the syntheses of biologically important alkaloids. Curr Top Med Chem.
2013;13(17):2184-99. doi: 10.2174/15680266113139990151. PMID:
23978134.
• González, J. M., Vidal, X., Ortuño, M. A., Mascareñas, J. L., & Gulías, M.
(2022). Chiral ligands based on binaphthyl scaffolds for Pd-catalyzed
enantioselective C-H activation/cycloaddition reactions. Journal of the
American Chemical Society, 144(47), 21437–21442.
https://doi.org/10.1021/jacs.2c09479
THANK YOU

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Chiral Ligand Role in Asymmetric Synthesis

  • 1. Chiral ligand and chiral induction Presented by- Sandeep Bindra
  • 2. Chiral ligand- • Chiral ligand are used in asymmetric synthesis. • Most of the chiral ligand combine with metals to form chiral catalyst. • Chiral catalyst engages in chemical reaction in which chirality is transfer to the reaction product. • If we want to create a new chiral center in a molecule, our starting material must have prochirality(the ability to become chiral in one simple transformation). • The most common prochiral units that give rise to new chiral centers are the trigonal carbon atom of alkenes and carbonyl groups, which become tetrahedral by addition reaction. • One of the simplest transformations you could imagine of a prochiral unit in to a chiral one is the reduction of ketone.
  • 3.
  • 4. • FIRST CATALYTIC SYMMETRIC SYNTHESIS- SYNTHESIS OF L-DOPA
  • 5.
  • 6. CHIRAL INDUCTION- It describe the formation of an excess of an enantiomer over the other from an achiral or racemic substrate using a chiral catalyst or chiral reagent is called chiral induction.
  • 7. EXAMPLES OF HOMOGENOUS CATALYSIS USED IN SYNTHESIS OF DRUGS- • Synthesis of L-DOPA-
  • 8. • Synthesis of (R) Naproxen- • Synthesis of S Ibuprofen-
  • 9. • Synthesis of (R) Citronellal-
  • 10. References- • Han, X., Zhang, J., Huang, J., Wu, X., Yuan, D., Liu, Y., & Cui, Y. (2018). Chiral induction in covalent organic frameworks. Nature Communications, 9(1). https://doi.org/10.1038/s41467-018-03689-9 • Pyarasani RD, John A, Santos LS. Recent developments of chiral induction in the syntheses of biologically important alkaloids. Curr Top Med Chem. 2013;13(17):2184-99. doi: 10.2174/15680266113139990151. PMID: 23978134. • González, J. M., Vidal, X., Ortuño, M. A., Mascareñas, J. L., & Gulías, M. (2022). Chiral ligands based on binaphthyl scaffolds for Pd-catalyzed enantioselective C-H activation/cycloaddition reactions. Journal of the American Chemical Society, 144(47), 21437–21442. https://doi.org/10.1021/jacs.2c09479