October 14, 2022 | Page 4 of 8 | Chiral phosphine ligands

Seo, Kyeongdeok’s team published research in Angewandte Chemie, International Edition in 2022-01-17 | 152140-65-3

Angewandte Chemie, International Edition published new progress about Aminoglycosides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Related Products of 152140-65-3.

Seo, Kyeongdeok; Jang, Seok Hyeon; Rhee, Young Ho published the artcile< Sequential Metal Catalysis towards 7-Oxostaurosporine and Its Non-Natural Septanose Analogue>, Related Products of 152140-65-3, the main research area is palladium catalyzed oxidative cyclization bicyclic aminoglycoside septanose oxostaurosporine preparation; septanose oxostaurosporine metal catalysis indolocarbazole alkoxyallene chemoselective addition synthon; Asymmetric synthesis; De novo synthesis; Indolocarbazole; Olefin migration; Total synthesis.

We report sequential metal catalysis towards indolocarbazole glycosides. The signature event is highlighted by (i) Pd0-catalyzed addition of indolocarbazole to alkoxyallene combined with ring-closing-metathesis; (ii) Ru-catalyzed chemoselective olefin migration; (iii) PdII-catalyzed oxidative cyclization to build the bicyclic core structure of the target compounds This approach gave access to both natural pyranose- and non-natural septanose glycosides. A short formal synthesis of 7-oxostaurosporine was achieved via this strategy.

Referemce:
Phosphine ligand,
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate

Webster, Robert’s team published research in Organic Letters in 2010-12-03 | 277306-29-3

Organic Letters published new progress about Chiral resolution (regiodivergent). 277306-29-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C32H40FeP2, Name: (2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene.

Webster, Robert; Boyer, Alistair; Fleming, Matthew J.; Lautens, Mark published the artcile< Practical Asymmetric Synthesis of Bioactive Aminotetralins from a Racemic Precursor Using a Regiodivergent Resolution>, Name: (2S)-1-[(1S)-1-[Bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene, the main research area is oxabicyclic alkene chiral rhodium catalyst amine ring opening; aminotetralin stereoselective preparation regiodivergent resolution; rotigotine stereoselective preparation.

Catalyst-controlled asym. ring opening of racemic oxabicyclic alkene I leads to two readily separable regioisomeric products, both in excellent ee. A cationic Rh catalyst, with added NH4BF4 to modulate reactivity, was required to obtain synthetically useful yields. The utility of each substituted aminotetralin product has been demonstrated by their conversion to the biol. relevant mols. Rotigotine and (S)-8-OH-DPAT in a highly efficient and practical manner.

Najera, Carmen’s team published research in Tetrahedron: Asymmetry in 2008-12-12 | 139139-93-8

Tetrahedron: Asymmetry published new progress about 1,3-Dipolar cycloaddition reaction, stereoselective. 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Related Products of 139139-93-8.

Najera, Carmen; de Gracia Retamosa, M.; Sansano, Jose M.; de Cozar, Abel; Cossio, Fernando P. published the artcile< Enantioselective synthesis of polysubstituted prolines by Binap-silver-catalyzed 1,3-dipolar cycloadditions>, Related Products of 139139-93-8, the main research area is polysubstituted proline derivative asym preparation; iminoester maleimide asym dipolar cycloaddition silver BINAP; silver BINAP asym dipolar cycloaddition catalyst.

The enantioselective 1,3-dipolar cycloaddition reaction of stabilized azomethine ylides, generated from iminoesters, with maleimides was efficiently achieved by intermediacy of an equimolar mixture of chiral (R)- or (S)-Binap and AgClO4. The high stability of the titled catalytic metal-complex to light exposure and its insolubility in toluene made possible its recovery and reutilization in other new process. In order to get a better understanding of the behavior of these chiral catalysts, we have carried out DFT1 calculations demonstrating the exptl. observed high enantio- and endo-selectivity through a very asynchronous transition state.

Shintani, Ryo’s team published research in Angewandte Chemie, International Edition in 2015 | 139139-86-9

Angewandte Chemie, International Edition published new progress about Alkynes, internal Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 139139-86-9 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Name: (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Shintani, Ryo; Takagi, Chihiro; Ito, Tomoaki; Naito, Masanobu; Nozaki, Kyoko published the artcile< Rhodium-Catalyzed Asymmetric Synthesis of Silicon-Stereogenic Dibenzosiloles by Enantioselective [2+2+2] Cycloaddition>, Name: (R)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl, the main research area is rhodium catalyzed asym synthesis silicon stereogenic dibenzosilole; enantioselective cycloaddition silyl prochiral triyne internal alkyne; germanium stereogenic dibenzogermole preparation; optical property dibenzosilole dibenzogermole; crystal mol structure alkynyl dibenzosilole; asymmetric catalysis; cycloaddition; dibenzosilole; rhodium; silicon.

A rhodium-catalyzed asym. synthesis of silicon-stereogenic dibenzosiloles has been developed through a [2+2+2] cycloaddition of silicon-containing prochiral triynes with internal alkynes. High yields and enantioselectivities have been achieved by employing an axially chiral monophosphine ligand, and the present catalysis is also applicable to the asym. synthesis of a germanium-stereogenic dibenzogermole. Preliminary studies on the optical properties of these compounds are also described.

Holzheimer, Mira’s team published research in Angewandte Chemie, International Edition in 2021-08-02 | 152140-65-3

Angewandte Chemie, International Edition published new progress about Absolute configuration. 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Product Details of C54H42N2O2P2.

Holzheimer, Mira; Sinninghe Damste, Jaap S.; Schouten, Stefan; Havenith, Remco W. A.; Cunha, Ana V.; Minnaard, Adriaan J. published the artcile< Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision>, Product Details of C54H42N2O2P2, the main research area is crenarchaeol total synthesis structure revision; macrocyclization total synthesis crenarchaeol; ring closing metathesis total synthesis crenarchaeol; archaea; crenarchaeol; structure revision; tetraether lipid; total synthesis.

Crenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane-spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic mol. in organic geochem. The 66-membered macrocycle possesses a unique chem. structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein, we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.

Arao, Takafumi’s team published research in Chemical & Pharmaceutical Bulletin in 2006-12-31 | 139139-93-8

Chemical & Pharmaceutical Bulletin published new progress about Arylation (intramol.). 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Name: (S)-(-)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl.

Arao, Takafumi; Kondo, Kazuhiro; Aoyama, Toyohiko published the artcile< Asymmetric construction of quaternary carbon stereocenter by Pd-catalyzed intramolecular α-arylation>, Name: (S)-(-)-2,2′-Bis(diphenylphosphino)-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-binaphthyl, the main research area is quaternary carbon stereocenter palladium catalyzed intramol arylation; enantioselective indolone preparation palladium catalyzed.

The catalyst comprised of Pd(OAc)2 and H8-BINAP provides good reaction conversions for a catalytic enantioselective intramol. α-arylation of N-(2-bromophenyl)-N-methyl-2-arylpropanamides. The corresponding 3-substituted indol-2-ones are formed with up to 68% enantioselectivity.

Das, Mrinal K’s team published research in Organic Letters in 2018-08-03 | 152140-65-3

Organic Letters published new progress about Allylation catalysts, stereoselective (decarboxylative). 152140-65-3 belongs to class chiral-phosphine-ligands, and the molecular formula is C54H42N2O2P2, Quality Control of 152140-65-3.

Das, Mrinal K.; Kumar, Nivesh; Bisai, Alakesh published the artcile< Catalytic Asymmetric Total Syntheses of Naturally Occurring Amarylidaceae Alkaloids, (-)-Crinine, (-)-epi-Crinine, (-)-Oxocrinine, (+)-epi-Elwesine, (+)-Vittatine, and (+)-epi-Vittatine>, Quality Control of 152140-65-3, the main research area is asym catalytic total synthesis Amaryllidaceae alkaloid; crinine catalytic asym total synthesis decarboxylative allylation; epi crinine catalytic asym total synthesis decarboxylative allylation; oxocrinine catalytic asym total synthesis decarboxylative allylation; elwesine epi catalytic asym total synthesis decarboxylative allylation; vittatine catalytic asym total synthesis decarboxylative allylation.

An expeditious approach to catalytic enantioselective total syntheses of crinine-type Amaryllidaceae alkaloids has been accomplished via a Pd-catalyzed enantioselective decarboxylative allylation of allylenol carbonates as a key step (up to 96% ee). Using this strategy, collective total syntheses of Amaryllidaceae alkaloids such as (-)-epi-elwesine I (R = OH, R1 = R2 = H), (-)-crinine I (R = H, R1 = OH, R22 = bond), (-)-epi-crinine I (R = OH, R1 = H, R22 = bond), (-)-oxocrinine I (RR1 = O, R22 = bond), and (-)-buphanisine I (R = H, R1 = OH, R22 = bond) have been accomplished. Gratifyingly, naturally occurring Amaryllidaceae alkaloids such as (+)-vittatine II (R = OH, R1 = H, R22 = bond), (+)-epi-vittatine II (R = H, R1 = OH, R22 = bond), and (+)-epi-elwesine II (R = R2 = H, R1 = OH) have also been achieved by switching the antipode of the ligand used in the catalytic enantioselective step.

Siu, Eulalia’s team published research in Biotechnology Progress in 2007-02-28 | 606-68-8

Biotechnology Progress published new progress about Electrochemical reduction. 606-68-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C21H27N7Na2O14P2, Reference of 606-68-8.

Siu, Eulalia; Won, Keehoon; Park, Chan Beum published the artcile< Electrochemical Regeneration of NADH Using Conductive Vanadia-Silica Xerogels>, Reference of 606-68-8, the main research area is electorchem NADH regeneration vanadia silica xerogel.

Elec. conductive sol-gel matrixes have been first introduced in order to enhance the efficiency of electrochem. NADH regeneration systems for biocatalysis. Vanadia-silica mixed gels as conductive sol-gels were synthesized using vanadium (V) oxytripropoxide (VOTP) and tetra-Me orthosilicate (TMOS) as precursors. Direct electrochem. reductions of NAD+ were carried out in the presence of vanadia-silica xerogels using unmodified platinum electrodes. Vanadia-silica gels from higher ratios of VOTP to TMOS could effectively improve electrochem. generations of NADH from NAD+. Direct electrochem. regenerations of NADH were coupled to the synthesis of L-glutamate from α-ketoglutarate catalyzed by glutamate dehydrogenases (GDH). In this case, vanadia-silica gels were used as matrixes for enzyme encapsulation, as opposed to serving as additives. When GDH were entrapped in “”nonconductive”” silica gels, synthesized using only TMOS, in the control experiment, the initial supply of NADH exhausted quickly and a final conversion of 30% was obtained. However, the use of conductive vanadia-silica gels with encapsulated GDH resulted in complete conversion of α-ketoglutarate to L-glutamate. A turnover number of a cofactor was also enhanced 3-fold by the application of conductive vanadia-silica gels.

Hida,Shoji’s team published research in Angewandte Chemie, International Edition in 2016 | 139139-93-8

Angewandte Chemie, International Edition published new progress about Aryl alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 139139-93-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C44H40P2, Electric Literature of 139139-93-8.

Kita, Yusuke; Hida, Shoji; Higashihara, Kenya; Jena, Himanshu Sekhar; Higashida, Kosuke; Mashima, Kazushi published the artcile< Chloride-Bridged Dinuclear Rhodium(III) Complexes Bearing Chiral Diphosphine Ligands: Catalyst Precursors for Asymmetric Hydrogenation of Simple Olefins>, Electric Literature of 139139-93-8, the main research area is diarylalkane enantioselective preparation; diarylalkene enantioselective hydrogenation rhodium catalyst; asymmetric catalysis; hydrogenation; reaction mechanisms; rhodium.

Efficient rhodium(III) catalysts were developed for asym. hydrogenation of simple olefins. A series of chloride-bridged dinuclear rhodium(III) complexes were synthesized from the rhodium(I) precursor [RhCl(cod)]2, chiral diphosphine ligands, and hydrochloric acid. Complexes from the series acted as efficient catalysts for asym. hydrogenation of (E)-prop-1-ene-1,2-diyldibenzene and its derivatives without any directing groups, in sharp contrast to widely used rhodium(I) catalytic systems that require a directing group for high enantioselectivity. The catalytic system was applied to asym. hydrogenation of allylic alcs., alkenylboranes, and unsaturated cyclic sulfones. Control experiments support the superiority of dinuclear rhodium(III) complexes over typical rhodium(I) catalytic systems.

Saba, Tony’s team published research in ACS Catalysis in 2021-01-01 | 606-68-8

ACS Catalysis published new progress about Hydrogenation. 606-68-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C21H27N7Na2O14P2, Formula: C21H27N7Na2O14P2.

Saba, Tony; Li, Jianwei; Burnett, Joseph W. H.; Howe, Russell F.; Kechagiopoulos, Panagiotis N.; Wang, Xiaodong published the artcile< NADH Regeneration: A Case Study of Pt-Catalyzed NAD+ Reduction with H2>, Formula: C21H27N7Na2O14P2, the main research area is TEM hydrogenation catalyst platinum; NAD hydrogenation NMR NADH platinum magnesium catalyst nicotinamide silica.

This study shows the importance of resolving catalytic performance in the regeneration of the reduced form of NAD (NADH) through activity measurements based on NAD+ conversion and the closure of mass balance via byproduct quantification. This approach is applied to assess the performance of supported platinum catalysts with varying points of zero charge, utilizing H2 as a reductant. It was found that Pt/SiO2, which exhibits a net neg. charge under the reaction conditions, outperforms the neutral Pt/C and pos. charged Pt/MgO because of the favorable electrostatic attraction between the catalyst surface and pos. charged (+1) nicotinamide ring. NMR spectroscopy identifies side-products formed during NAD+ hydrogenation.

ACS Catalysis published new progress about Hydrogenation. 606-68-8 belongs to class chiral-phosphine-ligands, and the molecular formula is C21H27N7Na2O14P2, Formula: C21H27N7Na2O14P2.