Date published: 2025-9-26

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(R,R)-DACH-phenyl Trost ligand (CAS 138517-61-0)

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Alternate Names:
(1R,2R)-(+)-1,2-Diaminocyclohexane-N,N′-bis(2-diphenylphosphinobenzoyl)
CAS Number:
138517-61-0
Molecular Weight:
690.75
Molecular Formula:
C44H40N2O2P2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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The (R,R)-DACH-phenyl Trost ligand represents a pinnacle in the field of asymmetric synthesis, embodying the fusion of chemistry and innovation. This ligand, characterized by its bis(diphenylphosphino)amine backbone where DACH stands for 1,2-diaminocyclohexane, is a cornerstone in the Trost asymmetric allylic alkylation reactions. It operates through a sophisticated mechanism where its chiral phosphorus atoms coordinate to transition metals, forming complexes that exhibit remarkable enantioselectivity during the allylation process. This unique ability to induce chirality in the resulting products without racemization is a testament to its precision and efficiency. In research, the (R,R)-DACH-phenyl Trost ligand has opened avenues for the synthesis of complex molecules with high enantiomeric excess, proving invaluable in the synthesis of natural products and active pharmaceutical ingredients. Its role extends beyond mere catalysis; it serves as a tool for understanding the subtleties of molecular interaction and stereochemistry, providing insights into the principles of asymmetric synthesis that are fundamental to advancing chemical science.


(R,R)-DACH-phenyl Trost ligand (CAS 138517-61-0) References

  1. Palladium-catalyzed allylic substitution with (η6-arene-CH2Z)Cr(CO)(3)-based nucleophiles.  |  Zhang, J., et al. 2011. J Am Chem Soc. 133: 20552-60. PMID: 22047504
  2. Enantioselective synthesis of 4-substituted tetrahydroisoquinolines via palladium-catalyzed intramolecular Friedel-Crafts type allylic alkylation of phenols.  |  Zhao, ZL., et al. 2015. Org Biomol Chem. 13: 3086-92. PMID: 25625805
  3. Enantioselective Total Syntheses of Akuammiline Alkaloids (+)-Strictamine, (-)-2(S)-Cathafoline, and (-)-Aspidophylline A.  |  Moreno, J., et al. 2016. J Am Chem Soc. 138: 1162-5. PMID: 26783944
  4. Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.  |  Hayashi, M., et al. 2016. European J Org Chem. 2016: 4800-4804. PMID: 28082832
  5. Enantioselective Total Syntheses of Methanoquinolizidine-Containing Akuammiline Alkaloids and Related Studies.  |  Picazo, E., et al. 2018. J Am Chem Soc. 140: 6483-6492. PMID: 29694031
  6. Development of an Enantioselective Allylic Alkylation of Acyclic α-Fluoro-β-ketoesters for Asymmetric Synthesis of 3-Fluoropiperidines.  |  Han, J., et al. 2022. Chemistry. 28: e202201595. PMID: 35815542
  7. Synthesis of macrocyclic nucleoside antibacterials and their interactions with MraY.  |  Nakaya, T., et al. 2022. Nat Commun. 13: 7575. PMID: 36539416

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

(R,R)-DACH-phenyl Trost ligand, 250 mg

sc-250838
250 mg
$144.00