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Copper/Guanidine-Catalyzed Asymmetric Alkynylation of Isatins

The highly enantioselective alkynylation of isatins, catalyzed by a bifunctional guanidine/CuI catalyst under mild reaction conditions, is described. The reaction is broad in scope with respect to alkyl/aryl-substituted terminal alkynes and substituted isatins, thus affording bioactive propargylic alcohols in excellent yields and enantioselectivities. Active duty: Asymmetric alkynylation of isatins was achieved by a new bifunctional chiral guanidine ligand in combination with CuI under mild reaction conditions. Good levels of reactivity and excellent enantioselectivities were achieved with diverse alkyl- and aryl-substituted terminal alkynes and various substituted isatins, thus generating bioactive 3-alkynyl-3-hydroxyindolin-2-ones.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Properties and Exciting Facts About 29841-69-8

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Probing the evolution of an Ar-BINMOL-derived salen-Co(iii) complex for asymmetric Henry reactions of aromatic aldehydes: Salan-Cu(ii) versus salen-Co(iii) catalysis

A new type of chiral salen-Co catalyst that features aromatic pi-walls and an active Co(iii) center has been developed for enantioselective Henry/nitroaldol reactions on the basis of salen-Cu catalysis. The asymmetric Henry reaction of aromatic aldehydes and nitromethane catalyzed by an Ar-BINMOL-derived salen-Co(iii) complex was achieved with high yields (up to 93%) and excellent enantioselectivities (up to 98% ee). And more interestingly, it was supposed that either salan-Cu(ii) or salen-Co(iii) complex-catalyzed Henry reaction was an ideal model reaction for providing direct evidence of noncovalent interaction due to the distinguishable ortho-substituted aromatic aldehydes from meta- or para-substituted benzaldehydes in terms of enantioselectivities and yields. the Partner Organisations 2014.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Improved Optical Resolution of (+/-)-1,2-Diphenylethylenediamine

(+/-)-1,2-Diphenylethylenediamine (DPEDA) was efficiently resolved by the fractional crystallization of its diastereomeric salts with optically active mandelic acid. 1H-NMR spectrum of N-monoacylated DPEDA with an optically active derivatizing agent showed that DPEDA thus obtained was optically pure.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Top Picks: new discover of (1S,2S)-(-)-1,2-Diphenylethylenediamine

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A Stereodynamic probe providing a chiroptical response to substrate-controlled induction of an axially chiral arylacetylene framework

A stereodynamic probe containing a central 1,4-di(phenylethynyl)benzene rod and two 2-formylphenylethynyl branches has been prepared through a series of Sonogashira cross-coupling reactions with 62% overall yield. This CD silent diarylacetylene-based framework carries two terminal aldehyde groups and provides a strong chiroptical response to substrate-controlled induction of three chiral axes upon diimine formation. The chiral amplification results in intense Cotton effects that can be used for in situ ICD analysis of the absolute configuration and ee of a wide range of amines.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions

The key factors for carbonyl-stabilised ammonium ylide-mediated epoxidation reactions were systematically investigated by experimental and computational means and the hereby obtained energy profiles provide explanations for the observed experimental results. In addition, we were able to identify the first tertiary amine-based chiral auxiliary that allows for high enantioselectivities and high yields for such epoxidation reactions.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Archives for Chemistry Experiments of 29841-69-8

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Preparation of polymer-supported Ru-TsDPEN catalysts and use for enantioselective synthesis of (S)-fluoxetine

Polymer-supported chiral ligands 9 and 17 were prepared based on Noyori’s (1S,2S)- or (1R,2R)-N-(p-tolylsulfonyl)-1,2-diphenylethylenediamine. The combination with [RuCl2(p-cymene)]2 has been shown to exhibit high activities and enantioselectivities for heterogeneous asymmetric transfer hydrogenation of aromatic ketones (19a-c) with formic acid-triethylamine azeotrope as the hydrogen donor, whereby affording the respective optically active alcohols 20a-c, the key precursors of chiral fluoxetine. As exemplified by ligand 17 for substrate 19c, the catalysts can be recovered and reused in three consecutive runs with no significant decline in enantioselectivity. The procedure avoids the plausible contamination of fluoxetine by the toxic transition metal species. The Royal Society of Chemistry 2005.

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Reference£º
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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29841-69-8, (1S,2S)-(-)-1,2-Diphenylethylenediamine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (S,S)-diphenylethylenediamine (250 mg, 1.2 mmol) and triethylamine (0.5 ml) in THF is added dropwise a solution of dansyl chloride (318 mg, 1.2 mmol) in THF (2 ml) at 0 C. After stirring 16 h at RT the solvent is removed in vacuum and the residue is resolved in methylenchloride (20 ml). The organic solution is washed with NaHCO3 solution (5 ml), dried over Na2SO4 and after filtration the solvent is removed. Flash chromatographie afford (S,S)-5-dimethylamino-naphthalene-1-sulfonic acid (2-amino-1,2-diphenyl-ethyl)-amide as yellow oil which crystallizes by drying in vacuum. M: 445.59. 1H-NMR (400 MHz, CDCl3):8.36 (t, J=7.5 Hz, 2 H), 8.17 (dd, J=7.2, 1.2 Hz, 1 H), 7.47 (dd, J=8.8 Hz, 1 H), 7.34 (dd, J=8.5 Hz, 1 H), 7.24-7.16 (m, 4 H), 7.11 (d, J=7.5 Hz, 1 H), 6.99-6.74 (m, 6 H), 4.61 (d, J=8.5 Hz, 1 H), 4.20 (d, J=8.5 Hz, 1 H), 2.80 (s, 6 H).

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Reference£º
Patent; Bilbe, Graeme; Cryan, John F.; Gentsch, Conrad; McAllister, Kevin Hall; Schmutz, Markus; Vassout, Annick; US2006/194791; (2006); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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(2); Synthesis of Rh+{2,2′-bis(diphenylphosphinyl)benzophenone} {(S,S)-DPEN}(SbF6-); Into [Rh+{2,2′-bis(diphenylphosphinyl)benzophenone}(cod)](SbF6-) obtained in the (1) after the distillation under reduced pressure were added 21.2 mg (0.1 mmol) of (S,S)-DPEN and 2 ml of methylene chloride, and then the solution was stirred under hydrogen atmosphere for 1 hour. The solvent was distilled off under reduced pressure and then the residue was dried to give 110 mg (yield: > 99%) of the title compound. 31p NMR (CDCl3) delta ppm; 48.28, 57.04 (2dd, Jp-p = 40.5 Hzo, Jp-Rh = 157.9 Hzo).

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Reference£º
Patent; Takasago International Corporation; EP1661903; (2006); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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29841-69-8, (1S,2S)-(-)-1,2-Diphenylethylenediamine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (S, S)-diphenylethylenediamine (250 mg, 1.2 mmol) and triethylamine (0.5 ml) in THF is added dropwise a solution of dansyl chloride (318 mg, 1.2 mmol) in THF (2 mi) at 0C. After stirring for 16 h at RT the solvent is removed in vacuum and the residue is resolved in methylenchloride (20 ml). The organic solution is washed with NaHCO3 solution (5 ml), dried over Na2SO4, and after filtration the solvent is removed. Flash chromatography affords (S, S)-5-dimethylamino-naphthalene-1-sulfonic acid (2-amino-1, 2-diphenyl-ethyl)- amide as yellow oil, which crystallizes by drying in vacuum. Molecular weight: 445. 59.’H- NMR (400 MHz, CDCI3) : 8.36 (t, J = 7.5 Hz, 2 H), 8.17 (dd, J = 7.2 Hz, 1.2 Hz, 1 H), 7.47 (dd, J = 8. 8 Hz, 1 H), 7.34 (dd, J = 8. 5 Hz, 1 H), 7.24-7. 16 (m, 4 H), 7.11 (d, J = 7. 5 Hz, 1 H), 6.99-6. 74 (m, 6 H), 4.61 (d, J = 8.5 Hz, 1 H), 4.20 (d, J = 8.5 Hz, 1 H), 2.80 (s, 6 H).

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Reference£º
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/92290; (2005); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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29841-69-8 (1S,2S)-(-)-1,2-Diphenylethylenediamine 6931238, acatalyst-ligand compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.29841-69-8,(1S,2S)-(-)-1,2-Diphenylethylenediamine,as a common compound, the synthetic route is as follows.

To a solution of (S,S)-diphenylethylenediamine (250 mg, 1.2 MMOL) and triethylamine (0.5 ml) in THF is added dropwise a solution of dansyl chloride (318 mg, 1.2 MMOL) in THF (2 ml) at 0 C. After stirring 16 h at RT the solvent is removed in vacuum and the residue is resolved in METHYLENCHLORIDE (20 ml). The organic solution is washed with NaHCO3 SOLUTION (5 ml), dried over Na2SO4 AND after filtration the solvent is removed. Flash chromatographie afford (S,S)-5-dimethylamino-naphthalene-1-sulfonic acid (2-amino-1,2- diphenyl-ethyl)-amide as yellow oil which crystallizes by drying in vacuum. M: 445. 59. 1H-NMR (400 MHz, CDCI3): 8.36 (t, J=7.5 Hz, 2H), 8.17 (dd, J=7.2, 1.2 Hz, 1H), 7.47 (dd, J=8.8 Hz, 1H), 7.34 (dd, J=8.5 Hz, 1H), 7.24-7.16 (m, 4 H), 7.11 (d, J=7.5 Hz, 1H), 6.99-6.74 (m, 6 H), 4.61 (d, J=8.5 Hz, 1 H), 4.20 (d, J=8.5Hz, 1 H), 2.80 (s, 6 H)., 29841-69-8

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Reference£º
Patent; Novartis AG; Novartis Pharma GmbH; WO2004/31155; (2004); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI