Category: 1192620-83-9

Bisset, Alexander A.; Dishington, Allan; Jones, Teyrnon; Clarkson, Guy J.; Wills, Martin published the artcile< Synthesis and reduction reactions of pyridones and 5-acyl-2-methoxypyridines>, Electric Literature of 1192620-83-9, the main research area is pyridine pyridinone preparation.

The synthesis of a series of pyridones, from their 2-hydroxypyridine or 2-methoxypyridine precursors, is described, along with studies into their reductions to saturated heterocycles. A number of 5-acyl-pyridones were prepared and were evaluated as substrates for asym. transfer hydrogenation prior to conversion to saturated heterocycles. The enantioselective reduction of 5-acetyl-1-benzyl-2,4(1H,3H)-pyrimidinedione is also described. The synthesis of the target compounds was achieved using [(R)-BINAP]ruthenium diacetate, [N-[(1R,2R)-1,2-diphenyl-2-[[3-(η6-phenyl)propyl](3-phenylpropyl)amino-κN]ethyl]-4-methylbenzenesulfonamidato-κN](chloro)ruthenium [N-[(1R,2R)-2-(amino-κN)-1,2-diphenylethyl]-4-methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5,6-η)-1-methyl-4-(1-methylethyl)benzene]ruthenium and [N-[(1S,2S)-1,2-diphenyl-2-[[3-(η6-phenyl)propyl](3-phenylpropyl)amino-κN]ethyl]-4-methylbenzenesulfonamidato-κN](chloro)ruthenium as catalysts. The title compounds thus formed included chiral 5-(1-hydroxyethyl)-2-piperidinone derivatives

Tetrahedron published new progress about Enantioselective synthesis. 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, Electric Literature of 1192620-83-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Bisset, Alexander A.; Shiibashi, Akira; Desmond, Jasmine L.; Dishington, Allan; Jones, Teyrnon; Clarkson, Guy J.; Ikariya, Takao; Wills, Martin published the artcile< Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione>, Quality Control of 1192620-83-9, the main research area is rhodium catalyst asym hydrogenation piperidinedione oxopyridinylmethylidene.

The synthesis of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione (I) from N-benzylglutarimide was achieved in three steps. The asym. hydrogenation of I gave either the product of partial reduction or full reduction, depending on the catalyst employed, with high ee in each case. Attempts at asym. transfer hydrogenation (ATH) of I resulted in formation of a racemic product.

Chemical Communications (Cambridge, United Kingdom) published new progress about Enantioselective synthesis. 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, Quality Control of 1192620-83-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Dub, Pavel A.; Tkachenko, Nikolay V.; Vyas, Vijyesh K.; Wills, Martin; Smith, Justin S.; Tretiak, Sergei published the artcile< Enantioselectivity in the Noyori-Ikariya Asymmetric Transfer Hydrogenation of Ketones>, Formula: C30H31ClN2O2RuS, the main research area is asym transfer hydrogenation ketone preparation chiral aralkyl alc cyclohexanemethanol; ruthenium arene chiral diamine catalyst asym transfer hydrogenation ketone.

Asym. transfer hydrogenation (ATH) is an important catalytic process in the fragrance and pharmaceutical industries. The Noyori-Ikariya chiral mol. ruthenium complex has been the catalyst of choice for this reaction for over 25 years. The mechanism and origin of enantioselectivity have irked chemists ever since the catalyst conception. This work addresses important shortcomings in understanding the origin of enantioselectivity with the Noyori-Ikariya catalysts, traditionally associated with the CH-π interaction. Here, we show that there are two spatial regions of the catalyst that simultaneously control the enantioselectivity for any arbitrary substrate: the region of the (tethered) η6-arene ligand and the region of the SO2 moiety. Dynamic equilibrium and interplay of attraction and repulsion via CH-π, C-H···H-C, lone pair-π, lone pair···H-C, and other noncovalent interactions in each region lead to stabilization/destabilization of the corresponding diastereomeric transition state and, as such, determine the final percent enantiomeric excess (% ee).

Organometallics published new progress about Aralkyl alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, Formula: C30H31ClN2O2RuS.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Chew, Renta Jonathan; Wills, Martin published the artcile< Exploitation of differential electronic densities for the stereoselective reduction of ketones bearing a masked amino surrogate>, Application In Synthesis of 1192620-83-9, the main research area is phthalimidyl ketoether preparation ruthenium catalyst enantioselective transfer hydrogenation; ether alc phthalimidyl preparation.

A tethered ruthenium-TsDPEN catalyst was employed for the facile catalytic asym. reduction of α-phthalimyl-α’-ketoethers under mild conditions. Leveraging exclusively on the contrasting electronic densities on the heteroatoms, a series of enantioenriched phthalimyl ether alcs. were obtained in generally good stereoselectivities from this challenging class of substrate. Subsequent transformation into highly valuable chiral β-amino alcs. was demonstrated to take place without significant losses in yield and optical purity.

Journal of Catalysis published new progress about Alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, Application In Synthesis of 1192620-83-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Dean, Conor; Rajkumar, Sundaram; Roesner, Stefan; Carson, Nessa; Clarkson, Guy J.; Wills, Martin; Jones, Matthew; Shipman, Michael published the artcile< Readily accessible sp3-rich cyclic hydrazine frameworks exploiting nitrogen fluxionality>, Synthetic Route of 1192620-83-9, the main research area is cyclic hydrazine preparation enantioselective principal moment inertia.

Here, a strategy for the creation of sp3-rich, non-planar heterocyclic scaffolds e.g., I suitable for drug discovery is described that obviates the need to generate multiple stereogenic centers with independent control. Asym. transfer hydrogenation using a tethered Ru-catalyst is used to efficiently produce a range of enantiopure cyclic hydrazine building blocks (up to 99% ee) e.g., I. Iterative C-N functionalization at the two nitrogen atoms of these compounds produces novel hydrazine and hydrazide based chem. libraries e.g., I. Wide chem. diversification is possible through variation in the hydrazine structure, use of different functionalization chemistries and coupling partners, and controlled engagement of each nitrogen of the hydrazine in turn. Principal Moment of Inertia (PMI) anal. of this small hydrazine library reveals excellent shape diversity and three-dimensionality. NMR and crystallog. studies confirm that the frameworks prefer to orient their substituents in three-dimensional space under the control of a single stereogenic center through exploitation of the fluxional behavior of the two nitrogen atoms.

Chemical Science published new progress about Aromatic alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, Synthetic Route of 1192620-83-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Cheung, Fung Kei; Clarke, Adam J.; Clarkson, Guy J.; Fox, David J.; Graham, Mark A.; Lin, Changxue; Criville, Adriana Lorente; Wills, Martin published the artcile< Kinetic and structural studies on tethered' Ru(ii) arene ketone reduction catalysts>, Synthetic Route of 1192620-83-9, the main research area is kinetic structure tethered ruthenium arene ketone reduction catalyst.

A series of kinetic and structural investigations on ruthenium-based catalysts for asym. transfer hydrogenation (ATH) of ketones are reported. A method is reported for monitoring the formation of ruthenium hydride species in real time using 1H NMR spectroscopy.

Dalton Transactions published new progress about Crystal structure. 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, Synthetic Route of 1192620-83-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Fang, Zhijia; Wills, Martin published the artcile< Asymmetric Transfer Hydrogenation of Functionalized Acetylenic Ketones>, HPLC of Formula: 1192620-83-9, the main research area is acetylenic ketone diketone ruthenium catalyzed stereoselective transfer hydrogenation; propargylic alc yashabushidiol B stereoselective preparation.

A systematic study of the asym. transfer hydrogenations of functionalized acetylenic ketones and diketones has been completed, together with a total synthesis of (S,S)-(-)-yashabushidiol B. In several cases, excellent enantioselectivities and yields were achieved.

Journal of Organic Chemistry published new progress about Alcohols, propargyl Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (chiral). 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, HPLC of Formula: 1192620-83-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Gediya, Shweta K.; Vyas, Vijyesh K.; Clarkson, Guy J.; Wills, Martin published the artcile< Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides>, COA of Formula: C30H31ClN2O2RuS, the main research area is hydroxydiamide regioselective enantioselective preparation; oxodiamide ruthenium chiral diamine catalyst asym transfer hydrogenation; hydroxyamide regioselective enantioselective preparation; oxoamide ruthenium chiral diamine catalyst asym transfer hydrogenation.

The asym. transfer hydrogenation (ATH) of α-keto-1,4-diamides using a tethered Ru/TsDPEN catalyst was achieved in high ee. Studies on derivatives identified the structural elements which led to the highest enantioselectivities in the products. The α-keto-amide reduction products were converted to a range of synthetically valuable derivatives

Organic Letters published new progress about Acetamides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, COA of Formula: C30H31ClN2O2RuS.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Mishra, Ashish A.; Bhanage, Bhalchandra M. published the artcile< Ru-Tethered (R,R)-TsDPEN with DMAB as an efficient catalytic system for high enantioselective one-pot synthesis of chiral β-aminol via asymmetric transfer hydrogenation>, Related Products of 1192620-83-9, the main research area is alpha substituted beta aminol enantioselective preparation; aniline alpha bromo ketone asym transfer hydrogenation ruthenium catalyst.

This work reflected Ru-tethered-TsDPEN as an active chiral catalyst for one pot selective synthesis of optically active α-substituted alcs. ArCH(OH)CH2NHAr1 [Ar = Ph, 2-FC6H4, 2,3-(MeO)2C6H3, etc.; Ar1 = Ph, 4-MeC6H4, 4-ClC6H4, 4-Cl-2-I-C6H3, etc.; stereo = S] and its derivatives from α-bromo ketones ArCOCH2Br in presence of dimethylamine borane (DMAB) as hydrogen source. Various Ru-chiral catalysts were screened and methodol. proceeded via a (R,R) Ru-tethered TsDPEN catalyst through asym. transfer hydrogenation (ATH) of in-situ formed ketones to corresponding chiral β-aminol product. Thus, Ru-tethered TsDPEN-DMAB catalytic system works efficiently with higher yield and high enantiomeric excess over others for ATH process. Based on a study of ortho, meta and para substituted α-bromo acetophenone derivatives, effective enantioselectivity was observed for ortho substituted β-aminol. The mechanism was optimized depending on product anal. with help of its kinetic AT-IR study. This work also focused on synthesis of various β-amino alc. derivatives where effect of an EWG and EDG on enantio-selectivity was studied.

New Journal of Chemistry published new progress about Amino alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, Related Products of 1192620-83-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Zheng, Ye; Wills, Martin published the artcile< Asymmetric transfer hydrogenation of boronic acid pinacol ester (Bpin)-containing acetophenones>, Related Products of 1192620-83-9, the main research area is boronic acid pinacol ester acetophenone enantioselective transfer hydrogenation; hydroxyethylphenyl boronic acid pinacol ester preparation haloarene palladium coupling; aryl phenylethanol preparation.

A series of Bpin-containing acetophenone derivatives were reduced by asym. transfer hydrogenation (ATH), using Noyori-Ikariya catalysts, with formic acid/triethylamine, to alcs. in high ee when the Bpin is in the para- or meta-position. Substrates containing ortho-Bpin groups were reduced in lower ee, with formation of a cyclic boron-containing group. The products were converted to substituted derivatives using Pd-catalyzed coupling reactions. The results represent the first examples of ATH of Bpin-containing ketones.

Organic & Biomolecular Chemistry published new progress about Aromatic alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 1192620-83-9 belongs to class amides-buliding-blocks, and the molecular formula is C30H31ClN2O2RuS, Related Products of 1192620-83-9.

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics