192461-80-6Relevant academic research and scientific papers
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.
TRICYCLIC GUANIDINE DERIVATIVE
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Paragraph 0228, (2016/04/19)
Disclosed are compounds useful as inhibitors of Phosphodiesterase 1 (PDE1), compositions thereof, and methods of using the same.
Zinc-catalyzed enantioselective hydrosilylation of imines
Park, Bu-Mahn,Mun, Soungyun,Yun, Jaesook
, p. 1029 - 1032 (2007/10/03)
The highly enantioselective reduction of imines is achieved by employing chiral Zn/diamine catalysts. This new catalytic protocol offers attractive features such as use of a non-precious metal and an inexpensive silane, easy modification of chiral diamine
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
Enantioselective borohydride reduction catalyzed by optically active cobalt complexes
Yamada, Tohru,Nagata, Takushi,Sugi, Kiyoaki D.,Yorozu, Kiyotaka,Ikeno, Taketo,Ohtsuka, Yuhki,Miyazaki, Daichi,Mukaiyama, Teruaki
, p. 4485 - 4509 (2007/10/03)
The highly enantioselective borohydride reduction of aromatic ketones or imines to the corresponding alcohols was developed in the presence of a catalytic amount of an optically active cobalt(II) complex catalyst. This enantioselective reduction is carried out using a precisely premodified borohydride with alcohols such as tetrahydrofurfuryl alcohol, ethanol and methanol. High optical yields are obtained by choosing the appropriate alcohol as modifiers and a suitable β-ketoiminato ligand of the catalyst. The enantioselective borohydride reduction has been successfully applied to the preparation of optically active 1,3-diols, the stereoselective reduction of diacylferrocenes, and dynamic and/or kinetic resolution of 1,3-dicarbonyl compounds.
A New Route To 1-Azaazulene Ring System By The Reaction Of 1-(Diphenylphosphinyl)azaallyl Anions With Tropone Derivatives
Ito, Koji,Nitta, Makoto
, p. 2247 - 2254 (2007/10/02)
The reaction of 1-(diphenylphosphinyl)azaallyl anions derived from the corresponding imines, with tropones underwent enamine-type alkylation and mainly followed by aza-Wittig reaction to give 1-azaazulene derivatives, in addition to a trace amount of 4H-4
