Tag: M.W=100-150

Wang, Runping published the artcileO2-Assisted Four-Component Reaction of Vinyl Magnesium Bromide with Chiral N-tert-Butanesulfinyl Imines To Form syn-1,3-Amino Alcohols, Synthetic Route of 343338-28-3, the main research area is syn aminoalc preparation diastereoselective; vinyl magnesium bromide tert butanesulfinyl imine four component oxygen; 1,3-amino alcohol; N-tert-butanesulfinyl imines; multi-component reaction; oxygenation; vinyl magnesium bromide.

An O2-assisted, four-component reaction has been developed to synthesize a wide range of syn-1,3-amino alcs. in one step. The reaction proceeds by oxygenation of vinyl magnesium bromide (component-I) with O2 (component-II) to give a magnesium enolate of acetaldehyde, which undergoes addition to a chiral N-tert-butanesulfinyl imine (component-III) followed by a sequential addition with excess vinyl magnesium bromide (component-IV). The approach allows diastereoselective synthesis of anti/syn- and syn/syn-3-amino-1,5-diols in good yields with high diastereoselectivity. The method was illustrated in an efficient, four-step synthesis of piperidine alkaloid (-)-2′-epi-ethylnorlobelol.

Angewandte Chemie, International Edition 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, Synthetic Route of 343338-28-3.

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

Li, Rui published the artcileCarbon-Sulfur Bond Formation: Tandem Process for the Synthesis of Functionalized Isothiazoles, Related Products of amides-buliding-blocks, the main research area is isothiazole preparation; aldehyde tert butanesulfinamide acetic anhydride tandem reaction.

In this paper, a new process for the construction of 3,4,5-substituted isothiazoles via reaction cascades including Pummerer-like rearrangement, nucleophilic condensation, and sulfenamide cyclization followed by concomitant elimination and dehydration under mild reaction conditions is reported. This process provides isothiazoles bearing fluorine and other functional groups in good to excellent yields from readily available starting materials.

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, Related Products of amides-buliding-blocks.

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

Appa, Rama Moorthy published the artcileFirst sonochemical, simple and solvent-free synthesis of chiral tert-butanesulfinimines using silica supported p-toluenesulfonic acid, COA of Formula: C4H11NOS, the main research area is tertiary butanesulfinamide aldehyde silica support toluenesulfonic acid sonochem synthesis; butanesulfinimine tertiary preparation green chem.

A solvent-free, versatile procedure was developed for the effective synthesis of tert-butanesulfinylimines of a variety of aldehydes using chiral tert-butanesulfinamides under green, sonochem. conditions. This method utilizes silica supported p-toluenesulfonic acid (pTSA·SiO2) as an efficient, safer and inexpensive catalyst under aerobic conditions. The practicable simplicity, easy preparation of the catalyst from readily available substances, high substrate scope, excellent yields of products in short reaction times and environmentally benign (solvent-free sonochem.) conditions were the exceptional assets of this finding.

Synthetic Communications 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, COA of Formula: C4H11NOS.

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

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