118949-61-4

Usage

Uses

Used in Catalyst Preparation:
(S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE is used as a ligand for the preparation of novel ruthenium-pyridine-carboxylate complexes. These complexes serve as new catalytic systems for alkene epoxidation, a significant reaction in organic chemistry for the synthesis of various chemical compounds and pharmaceuticals.
Used in Chemical Synthesis Industry:
In the chemical synthesis industry, (S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE is utilized as a chiral ligand to create enantioselective catalysts. These catalysts are essential for the production of enantiomerically pure compounds, which are crucial in pharmaceuticals, agrochemicals, and other specialty chemicals where the stereochemistry of a molecule can significantly impact its biological activity and efficacy.
Used in Research and Development:
(S,S)-2,6-BIS(4-ISOPROPYL-2-OXAZOLIN-2-YL)PYRIDINE is also used in research and development settings to explore its potential applications in asymmetric catalysis, enantioselective synthesis, and other areas of organic chemistry. Its unique structural features make it a valuable tool for chemists to study and develop new reactions and processes that can lead to innovative products and technologies.

Reaction

Ligand used in the dual-catalyst system for highly enantioselective conjugate cyanation of unsaturated imides. Ligand for cross-coupling reactions of iodoalkanes with alkyl zinc halides. Ligand for asymmetric 1,4-addition reactions of 1,3-dicarbonyl compounds to nitroalkenes. Ligand for asymmetric allylation of aldehydes with b-carbonyl allylstannanes. Ligand used in the enantioselective Negishi reaction of racemic secondary benzylic halides. Ligand for osmium catalyzed enantioselective transfer hydrogenation.

InChI:InChI=1/C17H23N3O2/c1-10(2)14-8-21-16(19-14)12-6-5-7-13(18-12)17-20-15(9-22-17)11(3)4/h5-7,10-11,14-15H,8-9H2,1-4H3/t14-,15-/m1/s1

Upstream product

• 329038-94-0 N²,N⁶-bis((S)-1-hydroxy-3-methylbutan-2-yl)pyridine-2,6-dicarboxamide 
• 5431-44-7 2,6-Pyridinedicarboxaldehyde 
• 2026-48-4 (S)-valinol 
• 55309-58-5 pyridine-2,6-dicarboximidic acid dimethyl ester 
• 626-05-1 2,6-Dibromopyridine 
• 132376-99-9 (S)-4-isopropyl-4,5-dihydrooxazole 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 2893-33-6 pyridine-2,6-dinitrile 
• 329038-95-1 Pyridine-2,6-dicarboxylic acid bis-[((S)-1-chloromethyl-2-methyl-propyl)-amide] 

Relevant academic research and scientific papers

Steric versus electronic effects of the ligand in the enantioselective palladium-catalyzed allylic alkylation with chiral oxazolinylpyridines

Chiral oxazolinylpyridines bearing an oxazolinyl [bis(oxazolinyl)pyridines] or a cyano group in the 6-position of the pyridine ring were prepared and assessed in the enantioselective palladium-catalyzed allylic substitution of 1,3-diphenylprop-2-enyl acet

An efficient and general one-pot method for the synthesis of chiral bis(oxazoline) and pyridine bis(oxazoline) ligands

An expeditious method for the synthesis of chiral box and pybox ligands is reported. The approach is based on a one-pot condensation reaction of chiral β-amino alcohols with a dinitrile using stoichiometric or catalytic amounts of zinc triflate. Yields gr

Secondary Phosphine Oxide Preligands for Palladium-Catalyzed C–H (Hetero)Arylations: Efficient Access to Pybox Ligands

C–H arylations of oxazolines were accomplished with a well-defined palladium catalyst derived from a secondary bisdiamantyl phosphine oxide. The single-component secondary phosphine oxide (SPO)-palladium complex enabled C–H activations with aryl bromides

Surfactant-Assisted Nanocrystalline Zinc Coordination Polymers: Controlled Particle Sizes and Synergistic Effects in Catalysis

Different morphologies and particle sizes of two crystalline zinc-based coordination polymers (CPs), [Zn(pytz)H2O]n (1; H2pytz=2,6-bis(tetrazole)pyridine) and [Zn2(pytz)24H2O] (2), from the bulk scale to the nanoscale, could be obtained under solvothermal conditions with different surfactants (polyvinylpyrrolidone (PVP) or polyethylene glycol (PEG) 2000) as templates. PVP and PEG 2000 could act as capping and structure-directing agents, respectively, to influence the growth of crystalline particles and control their sizes. CP 1 exhibits a two-dimensional framework with window-like units and 2 shows a bimetallic structure. Nanocrystalline 1 and 2 were used as heterogeneous catalysts to study how adjacent catalytic active sites synergistically effected their catalytic reactivities in the direct catalytic conversion of aromatic dinitriles into oxazolines. The results showed that 1 produced bis-oxazolines as the sole products, whereas 2 gave the mono-oxazolines as the major products under the same reaction conditions.

Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones

Control of stereochemistry in photocycloaddition reactions remains a substantial challenge; almost all successful catalytic examples to date have involved [2 + 2] photocycloadditions of enones. We report a method for the asymmetric [3 + 2] photocycloaddition of aryl cyclopropyl ketones that enables the enantiocontrolled construction of densely substituted cyclopentane structures not synthetically accessible using other catalytic methods. These results show that the dual-catalyst strategy developed in our laboratory broadens synthetic chemists' access to classes of photochemical cycloadditions that have not previously been feasible in enantioselective form.

Synthesis, characterization and 1,3-butadiene polymerization studies of cobalt dichloride complexes bearing pyridine bisoxazoline ligands

A series of ion-pair cobalt complexes bearing pyridine bisoxazoline ligands were successfully synthesized and characterized by IR spectroscopy and elemental analysis. Determined by X-ray crystallographic analysis, complexes 4a, 4b, 4e, and 4f existed as i

A Ce(OTf)3/PyBox catalyzed enantioselective Hosomi-Sakurai reaction of aldehydes with allyltrimethylsilane

An efficient enantioselective Hosomi-Sakurai reaction catalyzed by a chiral Ce(OTf)3/PyBox complex has been explored. In the presence of 20 mol% of a chiral catalytic complex prepared in situ from Ce(OTf)3 and 2,6-bis[(S)-4-isopropyl

Synthesis of optically active, unnatural α-substituted glutamic acid derivatives by a chiral calcium-catalyzed 1,4-addition reaction

The first catalytic asymmetric 1,4-addition reactions of azlactones with acrylic esters have been developed. A chiral coordinative calcium catalyst was found to be effective for these reactions, and the desired 1,4-adducts were obtained in good yields and enantioselectivities. The product was converted to the corresponding α-alkylated glutamic acid by acid hydrolysis.

Efficient oxidative synthesis of 2-oxazolines

New methodology for the synthesis of variously substituted 2-oxazolines and one dihydrooxazine using aldehydes, amino alcohols, and N-bromosuccinimide as an oxidizing agent is described. This one-pot synthesis is characterized by mild reaction conditions, broad scope, high yields, and its preparative simplicity. Georg Thieme Verlag Stuttgart.

Synthesis of asymmetric iron-pybox complexes and their application to aziridine forming reactions

The synthesis of a series of iron-pybox complexes and their employment in the catalytic asymmetric aziridine forming reaction is presented. When AgSbF6 is used as an initiator, the i-pr- and t-bu-pybox complexes produce 47% of the cis-aziridine