475110-11-3

Upstream product

• 158946-83-9 N,N'-bis[(S)-1-methoxycarbonyl-2-phenylethyl]-2,6-pyridinecarboxamide 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 
• 3182-95-4 L-Phenylalaninol 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 

Downstream Products

• 695228-49-0 N²,N⁶-bis[(S)-1-chloro-3-phenylpropan-2-yl]pyridine-2,6-dicarboxamide 
• 151670-69-8 2,6-bis<(S)-4'-benzyloxazolin-2'-yl>pyridine 

Relevant academic research and scientific papers

Synthesis and metal(II) ion complexation of pyridine-2, 6-diamides incorporating amino alcohols

Reaction of 2, 6-bis(methoxycarbonyl)pyridine with two equivalents of a-amino alcohol yields pyridine-2, 6-diamides C6H3N(CONH-CR1R2-CHR3-OH)2 [(1) R1 = R2 = R3 = H; (2) R1 = R 2 = H, R3 = CH3; (3) R1 = CH 3, R2 = R3 = H; (4) R1 = C 2H5, R2 = R3 = H; (5) R1 = C6H5CH2, R2 = R3 = H; (6) R1 = O2NC6H4CH(OH), R 2 = R3 = H; (7) R1 = R2 = CH 3, R3=H] incorporating the amino alcohols, several of which are chiral, whereas the free diamide ligands show no capacity toward deprotonation up to >pH 12. In the presence of metal(II) ions they undergo concomitant deprotonation and complexation to form [M(L-2H)] compounds. Formation constants have been determined for Cu(II), Ni(II), and Zn(II) complexes of the suite of ligands. Determined values for the two observed steps of log βML-2H and log βML-3H (where additional alcohol or coordinated water deprotonation occurs) are approximately-10 and-20, respectively. As pKa values of the diamide cannot be determined independently, absolute log KML-2H values for the di-deprotonated complexes cannot be definitively assigned, although estimates are made using predicted pKa values for the diamide. The circular dichroism spectra of optically active complexes were determined and are discussed.

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

Macrocyclic compound as NMR chiral solvating agent for determination of enantiomeric excess of carboxylic acids

1HNMR studies demonstrated that chiral macrocycle 1 was a good chiral solvating agent, and was effective for the determination of the enantiomeric excess of a wide range of rac-carboxylic acids. Large nonequivalent chemical shifts (up to 0.125 ppm) can be

Rational design of sterically and electronically easily tunable chiral bisimidazolines and their applications in dual lewis acid/brensted base catalysis for highly enantioselective nitroaldol (Henry) reactions

A new addition to the rational design of sterically and electrically easily tunable chiral bis(imidazoline) ligands from chiral amino alcohols has been developed. Vast structural variation of chiral bis(imidazoline) ligands can be simply achieved by the choice of both the 1,2-amino alcohol and its N-1 R 1 substituent. A small library of chiral bisimidazolines (1a-h) has been constructed. The method has provided an easy and simplified route to a diverse set of air-stable and water-tolerant chiral bis(imidazoline) ligands on 10 g scales. The dual Lewis Acid/Bronsted base catalytic system generated from the (5)-1a/Cu(OTf)2 complex and Et3N was able to catalyze Henry reactions between aldehydes and nitromethane effectively at room temperature, and also to tolerate a wide scope of aldehydes with excellent enantiomeric excesses. Not only aromatic aldehydes but also aliphatic aldehydes afforded the nitroalcohol products, with enantiomeric excesses in the 93-98% range. This dual catalytic system is among the most effective systems so far reported for the asymmetric parent Henry reactions. This work also represents the first members of the class of chiral bisimidazolines to have been demonstrated to achieve excellent enantioselectivities.

Synthesis and structures of new chiral diamide-ester macrocycles

A series of new hetero-macrocyclic diamide-ester compounds (4a - 4z, 6a - 6b) were synthesized using 4-(dimethylamino)pyridine as catalyst and characterization by infrared spectra, nuclear magnetic resonance spectra, mass spectra and elemental analyses. The structures of 4e and meso 4b were determined by X-ray crystallography. The association constants of the compounds with various metal ions were determined by UV-visible spectroscopic titration, and showed a selective recognition for certain metal ions.

Synthesis of novel chiral macrolides and their antifungal activity

Nineteen chiral macrocyclic diamide-diester ligands were synthesized using a three step reaction. The synthesis utilized the condensation of dicarbonyl dichlorides with chiral 2-aminoethanol derivatives. The reaction was catalyzed in a dual catalyst system. Some of the compounds were found to display antifungal activity.