153880-57-0Relevant articles and documents
Efficient Access to Chiral 2-Oxazolidinones via Ni-Catalyzed Asymmetric Hydrogenation: Scope Study, Mechanistic Explanation, and Origin of Enantioselectivity
Dong, Xiu-Qin,Liu, Yuanhua,Wang, Heng,Wang, Minyan,Yang, Xuanliang,Yi, Zhiyuan,Yin, Congcong,Zhang, Xumu
, p. 11153 - 11161 (2020/11/23)
Cheap transition metal Ni-catalyzed asymmetric hydrogenation of 2-oxazolones was successfully developed, which provided an efficient synthetic strategy to prepare various chiral 2-oxazolidinones with 95%-99% yields and 97%->99% ee. The gram-scale hydrogenation could be proceeded well with >99% ee in the presence of low catalyst loading (up to 3350 TON). This Ni-catalyzed hydrogenation protocol demonstrated great synthetic utility, and the chiral 2-oxazolidinone product was easily converted to a variety of other important molecules in good yields and without loss of ee values, such as chiral dihydrothiophene-2(3H)-thione, amino alcohol, oxazoline ligand, and allenamide. Moreover, a series of deuterium labeling experiments, control experiments, and DFT calculations were conducted to illustrate a reasonable catalytic mechanism for this Ni-catalyzed asymmetric hydrogenation, which involved a tautomerization between the enamine and its isomer imine and then went through asymmetric 1,2-addition of Ni(II)-H to the preferred imine.
Enantioselective Synthesis of N-Benzylic Heterocycles: A Nickel and Photoredox Dual Catalysis Approach
Pezzetta, Cristofer,Bonifazi, Davide,Davidson, Robert W. M.
supporting information, p. 8957 - 8961 (2019/11/11)
Reported herein is a dual nickel- and photoredox-catalyzed modular approach for the preparation of enantioenriched N-benzylic heterocycles. α-Heterocyclic carboxylic acids, easily obtainable from common commercial material, are reported as suitable substrates for a decarboxylative strategy in conjunction with a chiral pyridine-oxazoline (PyOx) ligand, providing quick access to enantioenriched drug-like products. The presence of a directing group on the heterocyclic moiety is shown to be beneficial, affording improved stereoselectivity in a number of cases.
Efficacious and rapid metal- and solvent-free synthesis of enantiopure oxazolines
Hassani, Rym,Requet, Alexandre,Marque, Sylvain,Gaucher, Anne,Prim, Damien,Kacem, Yakdhane,Hassine, Bchir Ben
, p. 1275 - 1279 (2015/01/08)
A rapid and efficient synthesis of oxazolines was performed starting from various nitriles using microwave irradiation combined to metal- and solvent-free conditions to afford high to quantitative yields of the targeted heterocycles.
Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines
Malkov, Andrei V.,Stewart-Liddon, Angus J. P.,McGeoch, Grant D.,Ramirez-Lopez, Pedro,Kocovsky, Pavel
, p. 4864 - 4877 (2012/07/28)
A new family of Lewis basic 2-pyridyl oxazolines have been developed, which can act as efficient organocatalysts for the enantioselective reduction of prochiral aromatic ketones and ketimines with trichlorosilane, a readily available and inexpensive reagent. 1-Isoquinolyl oxazoline, derived from mandelic acid, was identified as the most efficient catalyst of the series, capable of delivering high enantioselectivities in the reduction of both ketones (up to 94% ee) and ketimines (up to 89% ee).
Synthesis and evaluation of the in vitro DNA-binding properties of chiral cis-dichloro(pyridyloxazoline)platinum(II) complexes
Dodd, David W.,Toews, Heather E.,Trevail, Michael J.,Jennings, Michael C.,Hudson, Robert H.E.,Jones, Nathan D.
scheme or table, p. 321 - 327 (2009/10/23)
A series of chiral cis-dichloro(pyridyloxazoline)platinum(II) and palladium(II) complexes were synthesized and their reactivity towards a defined sequence of single-stranded and double-stranded DNA was investigated in comparison to cisplatin. The compounds differed in the nature and absolute configuration of the substituent at the C4 position of the oxazoline ring. The DNA-binding ability of these compounds was evaluated by HPLC analysis, post metal exposure, of enzymatic digests of an undecamer duplex containing one putative metallation site. Polyacrylamide gel electrophoresis (PAGE) and thermal denaturation confirmed the results of the HPLC analysis, which showed that the stereochemistry and character of the substituent at the C4 position of the oxazoline ring had little effect on DNA binding, possibly due to the formation of monofunctional adducts.
Remote chiral induction in the organocatalytic hydrosilylation of aromatic ketones and ketimines
Malkov, Andrei V.,Stewart Liddon, Angus J. P.,Ramirez-Lopez, Pedro,Bendova, Lada,Haigh, David,Kocovsky, Pavel
, p. 1432 - 1435 (2007/10/03)
(Chemical Equation Presented) Lewis basic, metal-free pyridyloxazolines catalyze the reduction of prochiral aromatic ketones and ketimines with Cl 3SiH in good enantioselectivity (up to 94% ee). Arene-arene interactions between the substrate and the catalyst are likely to play a role in the enantiodifferentiation process.
