82944-84-1Relevant academic research and scientific papers
SUBSTITUTED PYRROLIDINE AMIDES III
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Paragraph 0132, (2020/07/25)
The invention relates to compounds according to general formula (I), which act as modulators of the glucocorticoid receptor and can be used in the treatment and/or prophylaxis of disorders which are at least partially mediated by the glucocorticoid receptor.
Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an Iron(II) P-NH-P′ Complex
Seo, Chris S. G.,Tannoux, Thibault,Smith, Samantha A. M.,Lough, Alan J.,Morris, Robert H.
, p. 12040 - 12049 (2019/10/02)
Chiral amines are key building blocks in synthetic chemistry with numerous applications in the agricultural and pharmaceutical industries. Asymmetric imine hydrogenation, particularly with iridium catalysts, is well developed. However, imine reduction still remains challenging in the context of replacing such a precious metal with a cheap, nontoxic, and environmentally friendly substitute such as iron. Here, we report that an unsymmetrical iron P-NH-P′ catalyst that was previously shown to be effective for the asymmetric hydrogenation of aryl ketones is also a very effective catalyst for the asymmetric hydrogenation of prochiral aryl imines activated with N-diphenylphosphinoyl or N-tosyl groups. The P-NH-P′ abbreviation stands for (S,S)-PPh2CHPhCHPhNHCH2CH2PiPr2. Density functional theory results suggest that, surprisingly, the NH group on the catalyst activates and orients the imine to hydride attack by hydrogen bonding to the PO or SO group on the imine nitrogen, as opposed to the imine nitrogen itself. This may explain why N-Ph and N-Bu imines are not hydrogenated.
Asymmetric Transfer Hydrogenation in Thermomorphic Microemulsions Based on Ionic Liquids
Hejazifar, Mahtab,Pálv?lgyi, ádám Márk,Bitai, Jacqueline,Lanaridi, Olga,Bica-Schr?der, Katharina
, p. 1841 - 1851 (2019/10/11)
A thermomorphic ionic-liquid-based microemulsion system was successfully applied for the Ru-catalyzed asymmetric transfer hydrogenation of ketones. On the basis of the temperature-dependent multiphase behavior of the targeted microemulsion, simple product separation as well as catalyst recycling could be realized. The use of water-soluble ligands improved the immobilization of the catalyst in the microemulsion phase and significantly decreased the catalyst leaching into the organic layer upon extraction of the product. Eventually, the optimized microemulsion system could be applied to a wide range of aromatic ketones that were reduced with good isolated yields (up to 98%) and enantioselectivities (up to 97%), while aliphatic ketones were less successful.
Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: Application to the ketimine nitro-Mannich reaction
Nunez, Marta G.,Farley, Alistair J. M.,Dixon, Darren J.
supporting information, p. 16348 - 16351 (2013/12/04)
The design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Bronsted base/H-bond-donor organocatalysts are reported. These catalysts incorporate a triaryliminophosphorane as the Bronsted basic moiety and are readily synthesized via a last step Staudinger reaction of a chiral organoazide and a triarylphosphine. Their application to the first general enantioselective organocatalytic nitro-Mannich reaction of nitromethane to unactivated ketone-derived imines allows the enantioselective construction of β-nitroamines possessing a fully substituted carbon atom. The reaction is amenable to multigram scale-up, and the products are useful for the synthesis of enantiopure 1,2-diamine and α-amino acid derivatives.
Activation of the Si-B Linkage: Copper-Catalyzed addition of nucleophilic silicon to imines
Vyas, Devendra J.,Froehlich, Roland,Oestreich, Martin
supporting information; experimental part, p. 2094 - 2097 (2011/06/22)
Activation of the Si-B bond through copper-catalyzed transmetalation quickly developed into a practical method to generate Cu-Si reagents These silicon nucleophiles cleanly add to aldehyde-derived imine electrophiles to form R-silylated amines in protic media, and no carbon-tonitrogen Brook-type rearrangement of the intermediate anion is observed. Aside from electron-withdrawing groups at the imine nitrogen atom, for example, SO2Tol and P(O)Ph2, previously delicate nitrogen substituents such as phenyl or benzhydryl are tolerated. The same protocol also allows the unprecedented addition to representative ketone-derived imines.
Enantioselective Strecker-type reaction of phosphinoyl ketimines catalyzed by a chiral Zr-bipyridyldiol catalyst
Chen, Yi-Jing,Chen, Chinpiao
experimental part, p. 2201 - 2209 (2009/04/05)
An enantioselective Strecker reaction of N-diphenylphosphinoyl ketimines with TMSCN employing a chiral zirconium complex formed from chiral bipyridyl diol 1 as catalyst is described. The catalytic efficiency of chiral ligand 1 with other Lewis acids was also explored. Higher yields (50-85%) with moderate to good enantioselectivities (30-80%) were achieved for a variety of N-diphenylphosphinoyl ketimines.
A convenient and practical method for the synthesis of N-thiophosphoryl aldimines and ketimines
Xu, Xinyuan,Wang, Chungui,Zhou, Zhenghong,Zeng, Zebing,Xinpeng, Ma,Zhao, Guofeng,Tang, Chuchi
, p. 238 - 244 (2008/09/19)
A convenient and practical method for the preparation of N-thiophosphoryl imines was developed through the thermal condensation of acetals with different thiophosphoramides at 120160°C.
Enantioselective MSPV reduction of ketimines using 2-propanol and (BINOL)AlIII
Graves, Christopher R.,Scheidt, Karl A.,Nguyen, SonBinh T.
, p. 1229 - 1232 (2007/10/03)
A highly enantioselective Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)AlIII/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93-98%) are observed for a wide ra
Catalytic asymmetric synthesis of α,α,α- trifluoromethylamines by the copper-catalyzed nucleophilic addition of diorganozinc reagents to imines
Lauzon, Caroline,Charette, Andre B.
, p. 2743 - 2745 (2007/10/03)
A copper-catalyzed asymmetric addition of diorganozinc reagents to N-phosphinoylimines has been developed for the synthesis of chiral α,α,α-trifluoromethylamines. The trifluoromethyl ketimines, generated in situ from the corresponding hemiaminals, led to
Enantioselective reduction of imines catalyzed by a rhenium(V)-oxo complex
Nolin, Kristine A.,Ahn, Richard W.,Toste, F. Dean
, p. 12462 - 12463 (2007/10/03)
An air- and moisture-tolerant enantioselective hydrosilylation of N-phosphinyl imines employing a chiral Re(V)-oxo complex as a catalyst is described. The chiral catalyst is a cyanobis(oxazoline) (CNbox)-ligated rhenium-oxo complex of the general formula
