(R,R)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine, also known as (R,R)-Jacobsen's ligand, is a chiral ligand that was developed by Dr. Eric N. Jacobsen, a prominent American chemist. It is a valuable catalyst in asymmetric synthesis, a branch of chemistry focused on the creation of molecules with specific spatial arrangements, particularly mirror-image isomers (enantiomers).
The ligand is a complex formed by coordinating two 3,5-di-tert-butylsalicylaldehyde groups to a 1,2-cyclohexanediamine core. This unique arrangement imparts chirality to the ligand, allowing it to selectively influence the stereochemistry of certain chemical reactions. The two salicylaldehyde groups provide a chiral environment around the metal center, facilitating enantioselective transformations.
(R,R)-Jacobsen's ligand is widely used in catalytic asymmetric reactions, such as epoxidation, cyclopropanation, and aminohydroxylation of alkenes. The ligand plays a crucial role in these reactions by promoting the formation of chiral products with high enantioselectivity. Its applications have a significant impact on the synthesis of pharmaceuticals, agrochemicals, and other complex molecules where chirality is essential for their biological activity.
Overall, (R,R)-Jacobsen's ligand is a powerful tool in modern organic synthesis, enabling chemists to create enantiomerically enriched compounds efficiently and selectively.
1. Chirality: (R,R)-Jacobsen's ligand is chiral, meaning it has a non-superimposable mirror image. This property allows it to induce chirality in metal-catalyzed reactions, leading to the formation of enantiomerically enriched products.
2. Asymmetric Induction: The ligand demonstrates excellent enantioselectivity in various asymmetric reactions. It can direct the reaction to produce one specific enantiomer of a chiral product with high selectivity, making it a valuable tool in asymmetric synthesis.
3. Versatility: (R,R)-Jacobsen's ligand is widely applicable in a range of asymmetric transformations, including epoxidation, cyclopropanation, and aminohydroxylation of alkenes. Its versatility enables the synthesis of diverse chiral compounds with various functionalities.
4. Catalytic Efficiency: The ligand acts as a catalyst in the reactions, and only a small amount is required to achieve significant enantioselectivity. This catalytic efficiency makes it cost-effective and environmentally friendly.
5. High Yield: The use of (R,R)-Jacobsen's ligand often results in high yields of the desired chiral products, ensuring efficient and practical synthetic processes.
6. Steric and Electronic Control: The unique structure of the ligand provides both steric and electronic control over the reaction, influencing the selectivity of the reaction and promoting the formation of specific enantiomers.
7. Synthetic Advantages: (R,R)-Jacobsen's ligand allows chemists to access enantiomerically enriched compounds in a more straightforward and efficient manner than traditional resolution methods.
1. Asymmetric Epoxidation
The ligand is widely used in asymmetric epoxidation reactions of alkenes, where it enables the synthesis of chiral epoxides with high enantioselectivity.
2. Asymmetric Cyclopropanation
(R,R)-Jacobsen's ligand is employed in asymmetric cyclopropanation reactions, allowing the selective formation of chiral cyclopropanes.
3. Asymmetric Aminohydroxylation
It is utilized in asymmetric aminohydroxylation reactions of alkenes, leading to the preparation of enantioenriched aminohydrin derivatives.
4. Asymmetric Aziridination
The ligand is applied in asymmetric aziridination reactions, which result in the formation of chiral aziridine products.
5. Enantioselective Transformations
(R,R)-Jacobsen's ligand is employed in various other enantioselective transformations, including dihydroxylation and amination reactions.
6. Pharmaceutical Synthesis
Due to its ability to induce chirality in reactions, the ligand plays a crucial role in the synthesis of chiral intermediates and building blocks for pharmaceuticals and other bioactive compounds.
7. Agrochemical Synthesis
The ligand is used in the preparation of chiral agrochemicals and other specialty chemicals.
8. Material Science
(R,R)-Jacobsen's ligand can also be employed in the preparation of chiral materials for applications in optoelectronics and catalytic materials.
| Product Name |
(R,R)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine |
| Cas No. |
135616-40-9 |
| Molecular Formula |
C36H54N2O2 |
| Molecular Weight |
546.84 |
| Appearance |
Yellow powder |
| Purity |
98% Min |
| Boiling point |
615.2 °C at 760 mmHg |
| Melting point |
205-207 °C(lit.) |
| Flash point |
421.6°C |
| Refractive index |
1.547 |
Storage: Keep container tightly closed. Take care to store in a cool and dark place, away from incompatibles.
Package: 50kg/bag or as per your particular request.
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