357209-32-6 Usage
Description
2,6-BIS((3AR,8AS)-8H-INDENO(1,2-D)OXAZO& is a white powder that serves as a versatile catalytic ligand in various chemical reactions. It is known for its ability to facilitate selective carbon-carbon bond cleavage and enantioselective transformations, making it a valuable component in the synthesis of complex organic molecules.
Uses
2,6-BIS((3AR,8AS)-8H-INDENO(1,2-D)OXAZO& is used as a catalytic ligand for several applications in the field of organic chemistry:
1. In the [3+2] cycloaddition of N-tosyl aziridines with electron-rich alkenes, it promotes selective carbon-carbon bond cleavage, leading to the formation of desired products with high efficiency and selectivity.
2. It is employed in enantioselective Mukaiyama-aldol reactions, where it helps achieve high enantiomeric excess and diastereoselectivity, enabling the synthesis of chiral molecules with a single handedness.
3. In enantioselective carbonyl-ene reactions, 2,6-BIS((3AR,8AS)-8H-INDENO(1,2-D)OXAZO& acts as a ligand to control the stereochemistry of the reaction, providing access to enantiomerically pure products.
4. It is used in Cu(I)-catalyzed asymmetric alkynylation of imino esters with terminal alkynes, where it enhances the enantioselectivity of the reaction, allowing for the preparation of chiral alkynyl amines.
5. In asymmetric three-component coupling reactions catalyzed by a Cu/pybox complex, 2,6-BIS((3AR,8AS)-8H-INDENO(1,2-D)OXAZO& plays a crucial role in achieving high levels of enantioselectivity and chemical yield.
6. It is also utilized in enantioselective Diels-Alder reactions, where it assists in the formation of chiral cyclohexene derivatives with high enantiomeric purity.
7. In Ni-catalyzed cross-coupling reactions, 2,6-BIS((3AR,8AS)-8H-INDENO(1,2-D)OXAZO& acts as a ligand to improve the enantioselectivity and efficiency of the reaction, enabling the synthesis of optically active biaryl compounds.
Used in Pharmaceutical Industry:
2,6-BIS((3AR,8AS)-8H-INDENO(1,2-D)OXAZO& is used as a chiral ligand for the synthesis of enantiomerically pure pharmaceutical compounds, which is essential for their biological activity and safety.
Used in Agrochemical Industry:
In the agrochemical industry, 2,6-BIS((3AR,8AS)-8H-INDENO(1,2-D)OXAZO& is used as a ligand for the enantioselective synthesis of chiral pesticides and agrochemicals, ensuring their effectiveness and reducing potential environmental impact.
Used in Material Science:
2,6-BIS((3AR,8AS)-8H-INDENO(1,2-D)OXAZO& is employed in the development of chiral materials with specific properties, such as optical activity or enhanced stability, which can be used in various applications, including sensors and advanced materials.
Check Digit Verification of cas no
The CAS Registry Mumber 357209-32-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,5,7,2,0 and 9 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 357209-32:
(8*3)+(7*5)+(6*7)+(5*2)+(4*0)+(3*9)+(2*3)+(1*2)=146
146 % 10 = 6
So 357209-32-6 is a valid CAS Registry Number.
InChI:InChI=1/C25H19N3O2/c1-3-8-16-14(6-1)12-20-22(16)27-24(29-20)18-10-5-11-19(26-18)25-28-23-17-9-4-2-7-15(17)13-21(23)30-25/h1-11,20-23H,12-13H2/t20-,21-,22+,23+/m0/s1
357209-32-6Relevant articles and documents
Catalytic asymmetric [3+2] annulation of allylsilanes with isatins: Synthesis of spirooxindoles
Hanhan, Nadine V.,Ball-Jones, Nicolas R.,Tran, Ngon T.,Franz, Annaliese K.
supporting information; experimental part, p. 989 - 992 (2012/03/08)
Silyl-inspired spirocycle: The title reaction is the first example of a catalytic asymmetric [3+2] annulation reaction with allylsilanes. The annulation reaction utilizes a chiral ScCl2(SbF6)/L catalyst and TMSCl as a promoter to aff
Kinetic resolution by copper-catalyzed azide-alkyne cycloaddition
Meng, Jun-Cai,Fokin, Valery V.,Finn
, p. 4543 - 4546 (2007/10/03)
The use of chiral pybox ligands imparts enantioselectivity to the Cu I-catalyzed azide-alkyne cycloaddition reaction, in the form of kinetic resolution of α-chiral azides and desymmetrization of gem-diazides. While levels of selectivity are modest, the results show unequivocally that the process benefits from ligand-accelerated catalysis.
Asymmetric ring opening of meso epoxides with TMSCN catalyzed by (pybox)lanthanide complexes.
Schaus,Jacobsen
, p. 1001 - 1004 (2007/10/03)
The asymmetric ring opening of meso epoxides with TMSCN is catalyzed by (pybox)YbCl3 complexes, yielding the beta-trimethylsilyloxy nitrile ring-opened products with good enantioselectivities (83-92% ee). The reaction exhibits a second-order kinetic depen
