128249-70-7

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine is used as a chiral ligand for the copper-catalyzed enantioselective arylation of N-arylated tetrahydroisoquinolines (THIQs) with arylboronic acids in the presence of a photoredox catalyst. This application is crucial in the synthesis of biologically active compounds and pharmaceuticals, as it allows for the selective formation of enantiomers, which can have different biological activities and reduce potential side effects.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine serves as a versatile chiral ligand that can be employed in various asymmetric catalytic reactions. Its unique structure and properties enable the selective formation of enantiomers, which is essential for the development of enantiomerically pure compounds with specific biological activities and reduced side effects.
Used in Research and Development:
2,6-Bis[(4R)-4-phenyl-2-oxazolinyl]pyridine is also used in research and development for the exploration of new asymmetric catalytic reactions and the discovery of novel enantioselective synthetic methods. Its unique structure and properties make it a valuable tool for chemists to study and develop new reactions and applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

Reactions

Ligand for Copper catalyzed syn-selective Mukaiyama aldol reaction. Ligand for Tin catalyzed anti-selective aldol reaction. Ligand for Ytterbuim catalyzed desymmetrization of meso epoxides. Ligand for Copper catalyzed enantioselective addition of terminal alkynes to imines. Ligand for Scandium catalyzed enantioselective syn-selective ene reactions. Ligand for Copper catalysed asymmetric alkynylation of cyclic azomethine Imines. Ligand for Europium catalyzed asymmetric alpha amination.

InChI:InChI=1/C23H19N3O2/c1-3-8-16(9-4-1)20-14-27-22(25-20)18-12-7-13-19(24-18)23-26-21(15-28-23)17-10-5-2-6-11-17/h1-13,20-21H,14-15H2/t20-,21-/m1/s1

Upstream product

• 2893-33-6 pyridine-2,6-dinitrile 
• 56613-80-0 D-2-phenylglycinol 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 5431-44-7 2,6-Pyridinedicarboxaldehyde 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 
• 661464-60-4 N,N-bis((R)-2'-hydroxy-1'-phenylethyl)pyridine-2,6-dicarboxamide 

Relevant academic research and scientific papers

Amino acid recognition of pyridine bis(oxazoline)-copper(II) complex in aqueous solvent

Enantioselective recognition of amino acids has been studied with C2-symmetric chiral pyridine bis(oxazoline)-copper(II) complexes at physiological pH condition. UV-visible titration revealed strong binding of submillimolar dissociation constan

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.

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

An efficient oxidative conversion of aldehydes into 2-substituted 2-oxazolines using 1,3-diiodo-5,5-dimethylhydantoin

Various aromatic and aliphatic aldehydes were converted into the corresponding 2-aryl and 2-alkyl-2-oxazolines, respectively, in good to high yields by reaction with 2-aminoethanol and 1,3-diiodo-5,5-dimethylhydantoin. Moreover, chiral bis-2-oxazolines, which can be used as chiral ligands in asymmetric synthesis, could be also prepared in moderate yields by the reaction of dialdehydes with (R)-(-)-2-phenylglycinol under the same conditions. Georg Thieme Verlag Stuttgart.

Asymmetric catalysis in a micro reactor - Ce, Yb and Lu catalysed enantioselective addition of trimethylsilyl cyanide to benzaldehyde

A T-shaped micro reactor was used for the optimisation of reaction conditions for the enantioselective silylcyanation of benzaldehyde catalysed by lanthanide-pybox complexes. Compared to a conventional batch procedure, higher conversion was observed within shorter reaction time. The micro reactor process involving Lu(III) afforded essentially the same enantioselectivity as the batch process (73 vs 76% ee), whereas the enantioselectivity was lower in the micro reactor for catalysts containing Yb(III) (53 compared to 72%). Ce(III) provided very low selectivity in both types of processes (1 and 11% ee, respectively). A study of the effect of additives showed that the enantioselectivity in the Yb catalysed reaction performed in the micro reactor could be increased to 66%, whereas only a minor improvement, to 78% ee, was observed in the reaction with Lu. Graphical Abstract.

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