185346-09-2

Basic information

• Product Name: (-)-2,6-BIS[2-[3AS-(2(3'AR*,8'AS*),3A,8A)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]]PYRIDINE
• Synonyms: (-)-2,6-Bis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazolin-2-yl]pyridine, min. 97% Indenyl-PYBOX;2,6-Bis((3aS,8aR)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)pyridine;2,6-Bis[(3aS,8aR)-(-)-8H-indeno[1,2-d]oxazolin-2-yl)]pyridine;(3aS,3'aS,8aR,8'aR)-2,2'-(2,6-pyridinediyl)bis[3a,8a-dihydro-8H-Indeno[1,2-d]oxazole;(-)-2,6-Bis[2-{3aS-(2(3'aR*,8'aS*),3aα,8aα)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole}]pyridine,97%;Ι(3aS,8aR)-in-pybox;Dimethlyammonium dichlorotri(μ-chloro)bis[(S)-(?)-2,2′-bis(dip-tolylphosphino)1,1′-binaphthyl]diruthenate(Ι
• CAS NO: 185346-09-2
• Molecular Formula: C25H19N3O2
• Molecular Weight: 393.44
• Product Categories: organic amine;BOX series;Chiral Nitrogen
• Mol File: 185346-09-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 265°C (dec.)
• Boiling Point: 633.0±55.0 °C(Predicted)
• Appearance: white to off-white/Powder
• Density: 1.50±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.35±0.20(Predicted)
• CAS DataBase Reference: (-)-2,6-BIS[2-[3AS-(2(3'AR*,8'AS*),3A,8A)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-2,6-BIS[2-[3AS-(2(3'AR*,8'AS*),3A,8A)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]]PYRIDINE(185346-09-2)
• EPA Substance Registry System: (-)-2,6-BIS[2-[3AS-(2(3'AR*,8'AS*),3A,8A)-3A,8A-DIHYDRO-8H-INDENO[1,2-D]OXAZOLE]]PYRIDINE(185346-09-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• WGK Germany: 3
• Hazardous Substances Data: 185346-09-2(Hazardous Substances Data)

Usage

Reaction

Ligand for Iridium-catalyzed enantio- and diastereoselective reductive aldol reactions Ligand for Scandium-catalyzed asymmetric Nazarov reactions Ligand for Scandium-catalyzed enantioselective pyrrole alkylations of α,β-unsaturated 2-acyl imidazoles Ligand for Scandium-catalyzed enantioselective Friedel-Crafts Alkylations Ligand for Nickel-catalyzed asymmetric cross-couplings of racemic propargyl groups with arylzinc reagents Ligand for Scandium-catalyzed enantioselective intramolecular carbonyl-ene reaction, the synthesis of (+)-triptophenolide Ligand for Scandium-catalyzed asymmetric synthesis of substituted 3-hydroxy-2-oxindoles Ligand for Indium-catalyzed enantio- and regioselective addition of pyrroles to isatins Ligand for Scandium-catalyzed asymmetric [3+2] annulation of allylsilanes with isatins in the synthesis of spirooxindoles Ligand for Scandium-catalyzed enantioselective allylation of isatins using allylsilanes Ligand for Scandium-catalyzed enantioselective carboannulation with allylsilanes

Chemical Properties

White powder

Uses

Reactant involved in synthesis of:Chiral ruthenium(II)-pybox complexes for use as intramolecular C-H amination catalystsBis(oxazolinyl_pyridine-scandium(III) triflate complex catalyst for enantioselective addition of pyrroles to indolesChiral N,N,N-tridentate pybos and pyboxazine ligands

Upstream product

• 2893-33-6 pyridine-2,6-dinitrile 
• 7480-35-5 (1S,2R)-1-amino-2-indanol 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 55309-58-5 pyridine-2,6-dicarboximidic acid dimethyl ester 

Relevant articles and documents

Catalytic asymmetric [3+2] annulation of allylsilanes with isatins: Synthesis of spirooxindoles

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

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.

Concise synthesis of conformationally constrained pybox ligands

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