(1S,2S)-(-)-1,2-Diaminocyclohexane-N,N'-bis(2-diphenylphosphinobenzoyl)
[CAS# 169689-05-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: (1S,2S)-(-)-1,2-Diaminocyclohexane-N,N'-bis(2-diphenylphosphinobenzoyl)
• Synonyms: (S,S)-DACH-phenyl Trost ligand
• Molecular Formula: C₄₄H₄₀N₂O₂P₂
• Molecular Weight: 690.75
• CAS Registry Number: 169689-05-8
• SMILES: C1CC[C@@H]([C@H](C1)NC(=O)C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)NC(=O)C5=CC=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7

Properties

• Melting point: 136-142 °C
• alpha: -134 ° (c=1 in methanol)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

chiral ligand. The synthesis of this ligand emerged from the need to develop better chiral ligands for asymmetric catalysis, aimed at enhancing catalytic reactions involving chiral centers.

In asymmetric synthesis, the ligand plays a crucial role in catalyzing reactions that produce enantiomerically pure compounds. Asymmetric catalysis is essential for manufacturing chiral molecules, which are critical in pharmaceuticals, agrochemicals, and fine chemicals. The ligand has shown excellent performance in enantioselective hydrogenation reactions, facilitating the formation of chiral centers with high selectivity. This is vital for creating complex molecules with specific stereochemistry.

The ligand is also valuable in cross-coupling reactions, which are fundamental in organic synthesis for forming carbon-carbon bonds. Its bidentate nature enhances the stability of transition metal complexes, thereby improving the efficiency of these reactions. For instance, (1S,2S)-(-)-1,2-Diaminocyclohexane-N,N'-bis(2-diphenylphosphinobenzoyl) has been used in palladium-catalyzed cross-coupling reactions to synthesize complex organic molecules with high precision.

The synthesis of this ligand involves the reaction of (1S,2S)-1,2-diaminocyclohexane with 2-diphenylphosphinobenzoic acid derivatives. Precise control of the reaction conditions is necessary to achieve high purity of the final product. Analytical techniques such as NMR spectroscopy and X-ray crystallography are employed to confirm the structure and purity of the compound.

Ongoing research continues to explore new applications for this ligand, expanding its use in various catalytic processes and complex organic syntheses. Its ability to facilitate high selectivity and efficiency in reactions underscores its importance in both academic research and industrial applications.

In summary, (1S,2S)-(-)-1,2-Diaminocyclohexane-N,N'-bis(2-diphenylphosphinobenzoyl) represents a major advancement in chiral ligands. Its introduction has significantly enhanced asymmetric catalysis, enabling efficient synthesis of chiral and complex molecules. The continued exploration of its applications highlights its vital role in contemporary chemistry.

References

2007. Synthesis of Communiol A. Synfacts, 3(5), 0489.
DOI: 10.1055/s-2007-968389

2008. Epoxide Ring Opening with Oxygen Nucleophiles. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-036-00704

2018. Palladium-Catalyzed Asymmetric Allylic Alkylation Strategies for the Synthesis of Acyclic Tetrasubstituted Stereocenters. Synthesis, 50(23), 4585-4599.
DOI: 10.1055/s-0037-1610386