74879-43-9Relevant academic research and scientific papers
Homoallylic amines as efficient chiral inducing frameworks in the conjugate addition of amides to α,β-unsaturated esters. An entry to enantio-enriched diversely substituted amines
Anani, Lilia,Behr, Jean-Bernard,Coelho, Aurélien,Machado-Rodrigues, Carine,Massicot, Fabien,Rogier, Johann,Vasse, Jean-Luc
supporting information, p. 2632 - 2636 (2020/04/17)
The diastereoselective conjugate addition of secondary homoallylamines, obtained in the enantioenriched form via allylmetallation of imines, to α,β-unsaturated esters is reported. This method allows access to valuable building blocks as well as heterocyclic skeletons, providing tertiary amines bearing two chains integrating a stereogenic center adjacent to the nitrogen atom.
Use of Hypervalent Iodine in the Synthesis of Isomeric Dihydrooxazoles
Carlucci, Claudia,Tota, Arianna,Colella, Marco,Ronamazzi, Giuseppe,Clarkson, Guy J.,Luisi, Renzo,Degennaro, Leonardo
, p. 428 - 436 (2018/06/11)
[Figure not available: see fulltext.] A convenient synthesis of 2- and/or 3-oxazolines has been developed depending on the structure and stereochemistry of the starting amino alcohol. PhI(OAc)2 acted as oxidant on the intermediate imine, as sup
Development of a metal-free amine oxidation method utilizing DEAD chemistry
Wang,Piva De Silva,Wiebe,Fehr,Davis
, p. 48848 - 48852 (2017/11/06)
Herein, we examine the oxidative abilities of azodicarboxylates for the conversion of amines to imines. This method provides access to synthetically useful imine intermediates including β-carbolines, quinazolines and N-heterocyclic carbene precursors. The ability to recover spent azodicarboxylate for regeneration and further use underscores the applicability and appeal of this protocol.
Design and synthesis of enantiomeric (R)- and (S)-copper(II) and diorganotin(IV)-based antitumor agents: Their in vitro DNA binding profile, cleavage efficiency and cytotoxicity studies
Arjmand, Farukh,Muddassir, Mohd.,Yousuf, Imtiyaz
, p. 62 - 71 (2014/06/09)
New chiral reduced Schiff base ligands (R)/(S)-2-(2-hydroxy-1- phenylethylaminomethyl)phenol (L), (R)/(S)-2-(benzylamino)-2-phenylethanol (L′) and their Cu(II)/organotin(IV) complexes (1-4) were synthesized and thoroughly characterized. Preliminary in vit
Stereoselective synthesis of γ-lactams from imines and cyanosuccinic anhydrides
Tan, Darlene Q.,Younai, Ashkaan,Pattawong, Ommidala,Fettinger, James C.,Cheong, Paul Ha-Yeon,Shaw, Jared T.
supporting information, p. 5126 - 5129 (2013/10/22)
A reaction between imines and anhydrides has been developed with chiral disubstituted anhydrides and chiral imines. The synthesis of highly substituted γ-lactams with three stereogenic centers, including one quaternary center, proceeds at room temperature in high yield and with high diastereoselectivity in most cases. Enantiomerically pure alkyl-substituted anhydrides proceed with no epimerization, thus providing access to enantiomerically pure penta-substituted lactam products.
Double stereodifferentiation in the catalytic asymmetric aziridination of imines prepared from α-chiral amines
Huang, Li,Zhang, Yu,Staples, Richard J.,Huang, Rui H.,Wulff, William D.
supporting information; experimental part, p. 5302 - 5313 (2012/05/20)
The catalytic asymmetric aziridination of imines and diazo compounds (AZ reaction) mediated by boroxinate catalysts derived from the VANOL and VAPOL ligands was investigated with chiral imines derived from five different chiral, disubstituted, methyl amines. The strongest matched and mismatched reactions with the two enantiomers of the catalyst were noted with disubstituted methyl amines that had one aromatic and one aliphatic substituent. The synthetic scope for the AZ reaction was examined in detail for α-methylbenzyl amine for cis-aziridines from α-diazo esters and for trans-aziridines from α-diazo acetamides. Optically pure aziridines could be routinely obtained in good yields and with high diastereoselectivity and the minor diastereomer (if any) could be easily separated. The matched case for cis-aziridines involved the (R)-amine with the (S)-ligand, but curiously, for trans-aziridines the matched case involved the (R)-amine with the (R)-ligand for imines derived from benzaldehyde and n-butanal, and the (R)-amine with the (S)-ligand for imines derived from the bulkier aliphatic aldehydes pivaldehyde and cyclohexane carboxaldehyde.
Chemoselective organocatalytic aerobic oxidation of primary amines to secondary imines
Wendlandt, Alison E.,Stahl, Shannon S.
supporting information; experimental part, p. 2850 - 2853 (2012/07/17)
Biomimetic aerobic oxidation of primary benzylic amines has been achieved by using a quinone catalyst. Excellent selectivity is observed for primary, unbranched benzylic amines relative to secondary/tertiary amines, branched benzylic amines, and aliphatic amines. The exquisite selectivity for benzylic amines enables oxidative self-sorting within dynamic mixtures of amines and imines to afford high yields of cross-coupled imine products.
N-heterocyclic pyridylmethylamines: Synthesis, complexation, molecular structure, and application to asymmetric Suzuki-Miyaura and oxidative coupling reactions
Grach, Guillaume,Pieters, Gregory,Dinut, Aurelia,Terrasson, Vincent,Medimagh, Raouf,Bridoux, Alexandre,Razafimahaleo, Vanessa,Gaucher, Anne,Marque, Sylvain,Marrot, Jerome,Prim, Damien,Gil, Richard,Planas, Jose Giner,Vinas, Clara,Thomas, Isabelle,Roblin, Jean-Philippe,Troin, Yves
experimental part, p. 4074 - 4086 (2011/10/03)
The synthesis of N,N-bidentate ligands based on a π-deficient N-heterocyclic pyridylmethylamine core is described. The preparation and characterization of the corresponding N,N-ligand-palladium complexes in solution and the solid state are illustrated. Pd complexes showed a good yield and moderate catalytic activity (up to 40% ee) in the asymmetric Suzuki-Miyaura coupling reaction, leading to methoxybinaphthyl derivatives. The combination of N,N-pyridylmethylamines with cuprous iodide revealed effective catalytic systems in oxidative naphthol derivative coupling reactions, affording the corresponding binaphthyls in high yields and with enantioselectivities of up to 61%.
Sulfonic acid supported on hydroxyapatite-encapsulated-γ-Fe 2O3 nanocrystallites as a magnetically separable catalyst for one-pot reductive amination of carbonyl compounds
Deng, Jia,Mo, Li-Ping,Zhao, Fei-Yang,Hou, Lan-Lan,Yang, Li,Zhang, Zhan-Hui
experimental part, p. 2576 - 2584 (2011/10/18)
A novel, environmentally friendly procedure has been developed for the preparation of secondary or tertiary amines by one-pot reductive amination of carbonyl compounds using sodium borohydride in the presence of a magnetically recoverable sulfonic acid supported on hydroxyapatite-encapsulated-γ- Fe2O3 [γ-Fe2O3@HAP-SO 3H] at room temperature. The catalyst was easily separated from the reaction mixture by applying an external magnet and reused for six cycles without significant loss of catalytic activity.
Pyridine containing chiral macrocycles: Synthesis and their enantiomeric recognition for amino acid derivatives
Deniz, Pinar,Turgut, Yilmaz,Togrul, Mahmut,Hosgoren, Halil
, p. 6227 - 6232 (2011/09/19)
Four novel C2-symmetric enantiomerically pure, chiral pyridine-18-crown-6 type macrocycles containing lipophilic chains at the stereogenic centers were prepared. The enantioselectivity of the new ligands toward the enantiomers of d-,l-amino acid methyl ester derivatives were also determined by 1H NMR titration method. These novel macrocycles have been showed to be strong complexing agents for d- and l-amino acid methyl ester hydrochloride salts (with Kass up to 13590 M-1 and G 0 up to 23.3 kJ mol-1 and selectivity ratio: 80:20) by 1H NMR titration methods. These macrocyclic hosts exhibited enantioselective binding towards the d-enantiomer of valine methyl ester hydrochloride with Kd/Kl up to 5.08 in CDCl3 with 0.25% CD3OD.
