Category: 343338-28-3

Wei, Kai published the artcileSynthesis of Highly Functionalized Pyridines: A Metal-Free Cascade Process, HPLC of Formula: 343338-28-3, the main research area is dimethyl dioxinopyridinone preparation; tert butanesulfinamide aldehyde dioxinone tandem; Pummerer rearrangement aza Prins cyclization aromatization.

Herein, a new process for the synthesis of highly functionalized pyridines I (R = c-Bu, 4-ClC6H4, 3-furyl, etc.; R1 = H, Et, Ph, allyl) based on a tandem Pummerer-type rearrangement, aza-Prins cyclization, and elimination-induced aromatization is reported. This formal [5+1] cyclization provides pyridines in good yields with easily accessible starting materials. The synthetic potential of this new method is further demonstrated in the modification of the frameworks of BINOL and some natural products.

Organic Letters published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, HPLC of Formula: 343338-28-3.

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

Proietti, Giampiero published the artcileAccessing Perfluoroaryl Sulfonimidamides and Sulfoximines via Photogenerated Perfluoroaryl Nitrenes: Synthesis and Application as a Chiral Auxiliary, Product Details of C4H11NOS, the main research area is perfluoroaryl sulfonimidamide photochem preparation; perfluorinated azide sulfinamide photochem coupling; sulfoximine perfluoroaryl photochem preparation; sulfoxide perfluorinated azide photochem coupling.

A light-promoted generation of perfluorinated aromatic nitrenes, from perfluorinated azides, that subsequently were allowed to react with sulfinamides and sulfoxides, generating achiral and chiral sulfonimidamides (SIAs) and sulfoximines (SOIs). One of enantiopure SIAs was evaluated as a novel chiral auxiliary in Grignard additions to imines yielding product in up to 96:4 diastereomeric ratio.

Journal of Organic Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Product Details of C4H11NOS.

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

Li, Guozhu published the artcileIntroducing the Chiral Transient Directing Group Strategy to Rhodium(III)-Catalyzed Asymmetric C-H Activation, Application of (S)-2-Methylpropane-2-sulfinamide, the main research area is phthalide preparation chemoselective regioselective enantioselective; aldehyde CH activation chiral amine catalyst achiral rhodium; C−H activation; asymmetric catalysis; chiral transient directing group; phthalide; rhodium(III).

The chiral transient directing group (TDG) strategy was successfully introduced to the rhodium(III)-catalyzed asym. C-H activation. In the presence of a catalytic amount of a chiral amine and an achiral rhodium catalyst, various chiral phthalides such as I [R1 = H, 5-Me, 4,6-di-MeO, etc.; R2 = H, 2-F, 3,5-di-CF3, etc.] were synthesized from simple aldehydes with high chemoselectivity, regioselectivity and enantioselectivity (53 examples, up to 73% yield and >99% ee). It was noteworthy that the chiral induction model was different from the previously reported chiral TDG system using amino acid derivatives and palladium salts. The imino group generated in situ from chiral amine and aldehyde acted as the monodentate TDG to promote the C-H activation, stereoselectively generating the chiral rhodacycle bearing a chiral metal center. Moreover, the stereogenic center of the product was created and stereocontrolled during the Grignard-type addition of the C-Rh bond to aldehyde, rather than during the C-H activation step.

Chemistry – A European Journal published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Application of (S)-2-Methylpropane-2-sulfinamide.

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

Yisimayili, Nuermaimaiti published the artcileStereodivergent Construction of Vicinal Acyclic Quaternary-Tertiary Carbon Stereocenters by Michael-Type Alkylation of α,α-Disubstituted N-tert-Butanesulfinyl Ketimines, Product Details of C4H11NOS, the main research area is tert butanesulfinyl ketimine nitroalkene diastereoselective aza enolization conjugate addition; nitroalkyl tert butanesulfinyl ketimine preparation.

Vicinal quaternary-tertiary carbon stereocenters were constructed with excellent stereoselectivity via aza-enolization of enantioenriched acyclic N-tert-butanesulfinyl ketimines bearing two sterically similar α-linear alkyl substituents followed by conjugate addition to nitroalkenes. Further changes of the absolute configuration of the sulfinyl group and/or the α-stereocenter in the ketimine allowed the facile stereodivergent synthesis of all four diastereomers of the Michael-type alkylation adducts. This reaction is a successful example of acyclic stereocontrol based on stereoselective α-deprotonation for the formation of fully substituted aza-enolates from ketone derivatives

Organic Letters published new progress about Alkenes, nitro Role: RCT (Reactant), RACT (Reactant or Reagent). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Product Details of C4H11NOS.

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

Vazquez-Chavez, Josue published the artcileThe effect of chiral N-substituents with methyl or trifluoromethyl groups on the catalytic performance of mono- and bifunctional thioureas, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is ketoester unsaturated aldehyde thiourea chiral Michael addition catalyst oxidation; dihydropyran stereoselective preparation; enone aldehyde thiourea chiral baylis hillman reaction catalyst; hydroxymethyl enone preparation.

We evaluated thiourea organocatalysts that incorporate a chiral group which includes a trifluoromethyl moiety and contrasted their performance with non-fluorinated analogs. The comparison between such systems allows the direct study of the NH acidity of a thiourea bonded to an aliphatic substituent. In principle, -CF3 systems feature an enhanced hydrogen bond (HB) donor capacity that is undoubtedly beneficial for HB-catalysis applied to the Baylis-Hillman reaction. We found that the thiourea substituted on both nitrogens with this group accelerates this reaction like Schreiner’s thiourea. On the other hand, we observed a different behavior in reactions promoted by bifunctional catalysts (thiourea-primary amine). In the Michael addition of isobutyraldehyde to Me benzylidenepyruvate, the -CF3 containing catalysts were better than the -CH3 systems, whereas the conjugate addition to N-phenylmaleimide showed the opposite behavior. Theor. calculations of the transition states indicated that the phenylethyl group in fluorinated and non-fluorinated compounds have different kinds of interactions with the electrophile. These interactions are responsible for a different arrangement of the electrophile and thereby the selectivity of the catalyst. Therefore, it cannot be generalized that in all cases NH acidity correlates with the performance of the catalyst, particularly, with aliphatic substituents that unlike the aromatic ones possess groups that are outside the plane of the thiourea.

Organic & Biomolecular Chemistry published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide.

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

Wang, Lixian published the artcileAmino Acid Derived Chiral Aminobenzimidazole Manganese Catalysts for Asymmetric Transfer Hydrogenation of Ketones, Application of (S)-2-Methylpropane-2-sulfinamide, the main research area is ketone manganese chiral aminobenzimidazole asym transfer hydrogenation catalyst; alc stereoselective preparation.

A series of Mn(I) catalysts with chiral bidentate benzimidazoles derived from easily available amino acids has been developed. These types of phosphine-free chiral Mn catalysts demonstrate high activity and enantioselectivity in asym. transfer hydrogenation (ATH) for a broad range of ketone substrates. A bulkier substrate, such as 2,6-dichloro-3-fluoroacetophenone, can be converted into the drug intermediate alc. with up to 90% yield and 92% ee (e.g., crizotinib). On the basis of exptl. and DFT studies, a possible mechanism for this Mn-catalyzed ATH is also proposed. DFT calculations further render a plausible model for enantiocontrol in ketone hydrogenation, in which the π-π stacking interaction between the catalyst and the substrate plays an important role.

ACS Catalysis published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Application of (S)-2-Methylpropane-2-sulfinamide.

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

Francisco, Karol R. published the artcileStructure property relationships of N-acylsulfonamides and related bioisosteres, Application of (S)-2-Methylpropane-2-sulfinamide, the main research area is acylsulfonamide structure property relationship bioisostere; Bioisostere; Isosteric replacement; N-Acylsulfonamide isostere; Oxetane; Physicochemical properties; Structure property relationship (SPR); Thietane.

The N-acylsulfonamide functional group is a feature of the pharmacophore of several biol. active mols., including marketed drugs. Although this acidic moiety presents multiple points of attachments that could be exploited to introduce structural diversification, depending on the circumstances, the replacement of the functional group itself with a suitable surrogate, or bioisostere, may be desirable. A number of N-acylsulfonamide bioisosteres have been developed over the years that provide opportunities to modulate both structure and physicochem. properties of this important structural motif. To enable an assessment of the relative impact on physicochem. properties that these replacements may have compared to the N-acylsulfonamide group, we conducted a structure-property relationship study based on matched mol. pairs, in which the N-acylsulfonamide moiety of common template reference structures is replaced with a series of bioisosteres. The data presented, which include an assessment of relative changes in acidity, permeability, lipophilicity and intrinsic solubility, provides a basis for informed decisions when deploying N-acylsulfonamides, or surrogates thereof, in analog design.

European Journal of Medicinal Chemistry published new progress about Biological permeation (artificial membrane permeability assay). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Application of (S)-2-Methylpropane-2-sulfinamide.

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

Sharma, Hayden A. published the artcileEnantioselective catalytic 1,2-boronate rearrangements, Quality Control of 343338-28-3, the main research area is enantioselective boronate rearrangement boronic ester dichloromethane lithium ureaboronate catalyst; lithium urea boronate complex preparation catalyst boronate rearrangement dichloromethane; crystal structure lithium urea boronate complex; mol structure lithium urea boronate complex.

A strategy that facilitates the construction of a wide variety of trisubstituted stereocenters through a catalytically accessed common chiral intermediate could prove highly enabling for the field of synthetic chem. The authors report the discovery of enantioselective, catalytic 1,2-boronate rearrangements for the synthesis of α-chloro pinacol boronic esters from readily available boronic esters and CH2Cl2. The chiral building blocks produced in these reactions can undergo two sequential stereospecific elaborations to generate a wide assortment of trisubstituted stereocenters. The enantioselective reaction is catalyzed by a Li-isothiourea-boronate complex, which is proposed to promote rearrangement through a dual-Li-induced chloride abstraction orchestrated by Lewis basic functionality on the catalyst scaffold.

Science (Washington, DC, United States) published new progress about Addition reaction catalysts (Li-isothiourea-boronate complex). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Quality Control of 343338-28-3.

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

Cinelli, Maris A. published the artcileFirst Contact: 7-Phenyl-2-Aminoquinolines, Potent and Selective Neuronal Nitric Oxide Synthase Inhibitors That Target an Isoform-Specific Aspartate, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is phenyl aminoquinoline preparation neuronal nitric oxide synthase inhibitor human; mol docking SAR phenyl aminoquinoline crystal structure.

Inhibition of neuronal nitric oxide synthase (nNOS), an enzyme implicated in neurodegenerative disorders, is an attractive strategy for treating or preventing these diseases. Several classes of 2-aminoquinoline-based nNOS inhibitors were developed previously, but these compounds had drawbacks including off-target promiscuity, low activity against human nNOS, and only modest selectivity for nNOS over related enzymes. In this study, new nNOS inhibitors based on 7-phenyl-2-aminoquinoline were synthesized and assayed them against rat and human nNOS, human eNOS, and murine and (in some cases) human iNOS. Compounds with a meta-relationship between the aminoquinoline and a pos. charged tail moiety were potent and had up to nearly 900-fold selectivity for human nNOS over human eNOS. X-ray crystallog. indicates that the amino groups of some compounds occupy a water-filled pocket surrounding an nNOS-specific aspartate residue (absent in eNOS). This interaction was confirmed by mutagenesis studies, making 7-phenyl-2-aminoquinolines the first aminoquinolines to interact with this residue.

Journal of Medicinal Chemistry published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide.

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

Shan, Chao published the artcileConstruction of an α-chiral pyrrolidine library with a rapid and scalable continuous flow protocol, COA of Formula: C4H11NOS, the main research area is chloro tert butanesulfinyl imine grignard reagent continuous flow heterocyclization; tert butylsulfinyl pyrrolidine preparation enantioselective diastereoselective.

An α-chiral pyrrolidine library was established via a highly diastereoselective continuous flow protocol under mild conditions. Various functionalized pyrrolidines was obtained in generally high yields (up to 87%) and with superior diastereocontrol within 150 s. The utility of this flow methodol. was further demonstrated by the gram-scale preparation of a κ-opioid receptor selective antagonist Aticaprant intermediate. Moreover, the scale-up in a self-designed microfluidic reactor provided a throughput of 7.45 g h-1, suggesting its potential large-scale applications. The flow procedure afforded rapid, cost-efficient and scalable access to obtain chiral α-substituted pyrrolidines in the compound library.

Reaction Chemistry & Engineering published new progress about Bromoalkanes Role: RCT (Reactant), RACT (Reactant or Reagent). 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, COA of Formula: C4H11NOS.

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