CAS 135616-36-3 (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

(S,S)-(+)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine, with the CAS number 135616-36-3, is a chiral ligand used in coordination chemistry and catalysis. It is a Schiff base compound formed by the condensation of 3,5-di-tert-butylsalicylaldehyde with 1,2-cyclohexanediamine. The resulting compound exists in two enantiomeric forms: (S,S)-(+)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine and (R,R)-(-)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine, which are mirror images of each other.

This ligand is widely used in asymmetric catalysis due to its ability to coordinate with various transition metals, forming chiral complexes. These complexes can efficiently catalyze a wide range of organic reactions with high enantioselectivity, making them valuable in the synthesis of complex molecules and pharmaceutical intermediates.

As a chiral ligand, (S,S)-(+)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine plays a significant role in asymmetric synthesis, contributing to the advancement of various chemical processes in the field of organic chemistry. Researchers and chemists frequently employ this compound to design and develop new and efficient catalytic systems for the preparation of enantiomerically pure compounds.
1. Chiral Ligand: The compound is a chiral ligand, meaning it has a specific three-dimensional arrangement of atoms that gives rise to two mirror-image forms (enantiomers).

2. High Enantioselectivity: It exhibits high enantioselectivity when coordinated with transition metals to form chiral complexes. This property is essential for asymmetric catalysis, where the catalyst favors the formation of one enantiomer over the other.

3. Steric Hindrance: The tert-butyl groups attached to the aromatic rings of the ligand provide significant steric hindrance, which enhances its chiral recognition and selectivity in catalytic reactions.

4. Stability: (S,S)-(+)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine and its metal complexes are generally stable under the reaction conditions of various asymmetric catalytic processes.

5. Versatility: The ligand can coordinate with a wide range of transition metals, making it applicable in various asymmetric catalytic reactions, such as asymmetric hydrogenation, allylic substitution, and cyclopropanation.

6. Synthetic Utility: Due to its high enantioselectivity and efficiency in asymmetric catalysis, the compound has become a valuable tool in the synthesis of enantiomerically pure compounds, which are essential in pharmaceuticals, agrochemicals, and other fine chemicals.
1. Asymmetric Hydrogenation
(S,S)-Salen cobalt(II) is widely used as a chiral ligand in asymmetric hydrogenation reactions. It can efficiently catalyze the hydrogenation of prochiral olefins, leading to the formation of enantiomerically enriched products.

2. Allylic Substitution
The compound is utilized as a ligand in asymmetric allylic substitution reactions. It enables the asymmetric transfer of nucleophiles to allylic substrates, facilitating the formation of chiral compounds with high enantioselectivity.

3. Cyclopropanation
(S,S)-Salen cobalt(II) is employed in asymmetric cyclopropanation reactions. It promotes the formation of chiral cyclopropane derivatives with excellent stereochemical control.

4. Epoxidation
The ligand is utilized in asymmetric epoxidation reactions, enabling the formation of optically active epoxides.

5. Oxidative Amination
(S,S)-Salen cobalt(II) can be employed in asymmetric oxidative amination reactions, facilitating the synthesis of chiral amines with high enantioselectivity.

6. Kinetic Resolution
It can be used in kinetic resolution processes, where a racemic mixture of a substrate is selectively transformed into one enantiomer, leaving the other enantiomer unaffected.   

 

Storage: Inert atmosphere, room temperature.

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