Category: 343338-28-3

Turlik, Aneta published the artcileMechanism and Origins of Stereoselectivity of the Aldol-Tishchenko Reaction of Sulfinimines, COA of Formula: C4H11NOS, the main research area is sulfinimine stereoselective aldol Tishchenko reaction.

D. functional theory computations have elucidated the mechanism and origins of stereoselectivity in McGlacken’s aldol-Tishchenko reaction for the diastereoselective synthesis of 1,3-amino alcs. using Ellman’s t-butylsulfinimines as chiral auxiliaries. Variations of stereochem. outcome are dependent on the nature of the ketone starting materials used, and the aspects leading to these differences have been rationalized. The intramol. hydride transfer step is the rate- and stereochem.-determining step, and all prior steps are reversible.

Journal of Organic Chemistry published new progress about Aldol addition. 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

Tan, Tong-De published the artcileCopper-Catalyzed Cascade Cyclization of Indolyl Homopropargyl Amides: Stereospecific Construction of Bridged Aza-[n.2.1] Skeletons, SDS of cas: 343338-28-3, the main research area is copper catalyzed cascade cyclization indolyl homopropargyl amide; stereospecific synthesis bridged azabicycle; copper; cyclizations; heterocycles; stereoselectivity; synthetic methods.

Catalytic cycloisomerization-initiated cascade cyclizations of terminal alkynes have received tremendous interest, and been widely used in the facile synthesis of a diverse array of valuable complex heterocycles. However, these tandem reactions have been mostly limited to noble-metal catalysis, and are initiated by an exo-cyclization pathway. Reported herein is an unprecedented copper-catalyzed endo-cyclization-initiated tandem reaction of indolyl homopropargyl amides, where copper catalyzes both the hydroamination and Friedel-Crafts alkylation process [e.g., I �II (85%)]. This method allows the practical and atom-economical synthesis of valuable bridged aza-[n.2.1] skeletons (n=3-6) with wide substrate scope, and excellent diastereoselectivity and enantioselectivity by a chirality-transfer strategy. Moreover, the mechanistic rationale for this novel cascade cyclization is also strongly supported by control experiments, and is distinctively different from the related gold catalysis.

Angewandte Chemie, International Edition published new progress about Cyclization catalysts, stereoselective. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, SDS of cas: 343338-28-3.

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

Doler, Carina published the artcileStereoselective synthesis of chiral thiol-containing 1,2-aminoalcohols via SmI2-mediated coupling, Application of (S)-2-Methylpropane-2-sulfinamide, the main research area is aminohydroxythiol preparation enantioselective diastereoselective; aldehyde sulfinylimine reductive coupling samarium diiodide catalyst.

The stereoselective synthesis of highly functionalized aminohydroxythiols I (R = tert-Bu, iso-Pr, iso-Bu, benzyl; R1 = tritylthiomethyl, 2-(tritylthio)ethan-1-yl; R2 = H; R1R2 = -CH2SCH(Ph)-, -C(CH3)2SCH(Ph)-) represents a synthetic challenge as the oxidation sensitivity and coordinating property of the thiol group interferes with many established synthetic methods. The SmI2/LiBr-mediated reductive coupling between Ellman N-sulfinylimines, containing thiol groups protected either as trityl thioether or dihydrothiazolidine R1[NBoc (R2)]CHCH=NS(O)C(CH3)3, and aldehydes RCHO enables the synthesis of chiral aminohydroxythiols I in high enantio- and diastereoselectivity. The scope of this reaction has been established for eighteen examples and applied for the synthesis of intermediate A [(7S,8R)-7,8-diamino-6-hydroxy-9-mercaptononanoate] needed for a biosynthesis study.

Tetrahedron published new progress about Amino alcohols, chiral Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), 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

Hirano, Kazuki published the artcileDiastereoselective Synthesis of Enantioenriched Trifluoromethylated Ethylenediamines and Isoindolines Containing Two Stereogenic Carbon Centers by Nucleophilic Trifluoromethylation Using HFC-23, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is diastereoselective synthesis trifluoromethylated ethylenediamine; trifluoromethylated isoindoline diastereoselective synthesis; stereodivergent nucleophilic trifluoromethylation aza Michael sequence HFC23.

Fluoroform, HFC-23, is an industrial byproduct from the synthesis of polytetrafluoroethylene and is a vastly underused resource; however, its physicochem. properties have hindered progress toward synthetic uses. Herein, we describe the use of HFC-23 as a cheap trifluoromethylating agent in two reactions for the highly diastereoselective synthesis of medicinally attractive chiral amines with two stereogenic carbon centers: a base-dependent, stereodivergent nucleophilic addition to synthesize enantioenriched vicinal diamines and a tandem nucleophilic addition/aza-Michael sequence toward enantioenriched isoindolines.

Journal of Organic Chemistry published new progress about Aza-Michael reaction. 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

Delost, Michael D. published the artcileMild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is trifluoromethylthiolated aziridine cyclopropane preparation diastereoselective; vinyl ketone tosyl imine trifluoromethylthiolated bromo acetophenone Darzens annulation.

Authors report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to underwent [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.

Organic Letters published new progress about Aziridines 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

Lee, Byung Joo published the artcileSynthesis of Unsymmetrical Vicinal Diamines via Directed Hydroamination, Formula: C4H11NOS, the main research area is allylamine amine rhodium regioselective chemoselective diastereoselective hydroamination; vicinal diamine preparation.

The rhodium-catalyzed hydroamination of primary and secondary allylic amines using diverse amine nucleophiles, including primary, secondary, acyclic, and cyclic aliphatic amines to access a wide range of unsym. vicinal diamines, was presented. The utility of this methodol. was further demonstrated through the rapid synthesis of several bioactive mols. and analogs.

Organic Letters published new progress about Chemoselectivity. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Formula: C4H11NOS.

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

Charaschanya, Manwika published the artcileSynthesis and optimization of nitroxide-based inhibitors of ferroptotic cell death in cancer cells and macrophages, Synthetic Route of 343338-28-3, the main research area is alkene peptide isostere synthesis nitroxide inhibitor ferroptotic cell death; peptide alkene enantioselective diastereoselective synthesis antitumor structure activity ferroptosis; vinylogous Mannich reaction cross metathesis drug desigh luminescence.

JP4-039 Is an alkene peptide isostere that acts as a low-micromolar inhibitor of erastin- and RSL-3-induced ferroptotic cell death in the HT-1080 cell line. In this work, we have developed new synthetic strategies that allow access to analogs of this lead structure. Enantioselective vinylogous Mannich or cross-metathesis reactions were key to the preparation of a series of analogs that culminated in the preparation of the ca. 30-fold more potent analog (I) (BOC = tert-butoxycarbonyl). Structure-activity relationship analyses used both HT-1080 cells and a luminescence-based ferroptosis assay in RAW 264.7 macrophages. In particular, α,α-disubstituted alkene peptide isosteres (Rα ≠ H) were found to exceed the potency of the corresponding glycine (Rα = H) derivatives

ACS Medicinal Chemistry Letters published new progress about Antitumor agents. 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

Hugelshofer, Cedric L. published the artcileCalyciphylline B-Type Alkaloids: Total Syntheses of (-)-Daphlongamine H and (-)-Isodaphlongamine H, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is deoxyisocalyciphylline B structure revision; daphlongamine H total synthesis; isodaphlongamine H total synthesis; Mannich reaction daphlongamine H synthesis; cyclization daphlongamine H synthesis; diastereoselective hydrogenation daphlongamine H synthesis; Pauson Khand reaction daphlongamine H synthesis; calyciphylline B type alkaloid synthesis.

The first total synthesis of the complex hexacyclic Daphniphyllum alkaloid (-)-daphlongamine H (I; 5S,6R) has been accomplished. Key to the success of the strategy are a complexity-building Mannich reaction, efficient cyclizations, and a highly diastereoselective hydrogenation to assemble multigram quantities of the tricyclic core bearing four contiguous stereocenters. Following construction of the hydro-indene substructure by means of a Pauson-Khand reaction, endgame redox manipulations delivered the natural product. Importantly, the synthetic studies have also given access to (-)-isodaphlongamine H (II; 5R,6R) and led to a revision of the reported structure of deoxyisocalyciphylline B as daphlongamine H.

Journal of the American Chemical Society published new progress about Chiral auxiliary (Mannich reaction using sulfinyl imine chiral auxiliary). 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

Hamilton, Matthew M. published the artcileDiscovery of IACS-9779 and IACS-70465 as Potent Inhibitors Targeting Indoleamine 2,3-Dioxygenase 1 (IDO1) Apoenzyme, Application In Synthesis of 343338-28-3, the main research area is bicyclohexane preparation indoleamine dioxygenase 1 inhibitor structure activity; structure activity bicyclohexane indoleamine dioxygenase 1 inhibitor.

Indoleamine 2,3-dioxygenase 1 (IDO1), a heme-containing enzyme that mediates the rate-limiting step in the metabolism of L-tryptophan to kynurenine, has been widely explored as a potential immunotherapeutic target in oncol. The authors have developed a class of inhibitors with a conformationally constrained bicyclo[3.1.0]hexane core. These potently inhibited IDO1 in a cellular context by binding to the apoenzyme, as elucidated by biochem. characterization and X-ray crystallog. A SKOV3 tumor model was instrumental in differentiating compounds, leading to the identification of I (IACS-9779) and II (IACS-70465). IACS-70465 has excellent cellular potency, a robust pharmacodynamic response, and in a human whole blood assay was more potent than linrodostat (BMS-986205). IACS-9779 with a predicted human efficacious once-daily dose below 1 mg/kg to sustain >90% inhibition of IDO1 displayed an acceptable safety margin in rodent toxicol. and dog cardiovascular studies to support advancement into preclin. safety evaluation for human development.

Journal of Medicinal Chemistry published new progress about Crystal structure. 343338-28-3 belongs to class amides-buliding-blocks, name is (S)-2-Methylpropane-2-sulfinamide, and the molecular formula is C4H11NOS, Application In Synthesis of 343338-28-3.

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

Yoshinaga, Yukako published the artcileStereoinvertive C-C Bond Formation at the Boron-Bound Stereogenic Centers through Copper-Bipyridine-Catalyzed Intramolecular Coupling of α-Aminobenzylboronic Esters, Application of (S)-2-Methylpropane-2-sulfinamide, the main research area is bromobenzamidobenzylic boronate nonracemic preparation; isoindolinone nonracemic preparation; copper bipyridine catalyst intramol Suzuki coupling bromobenzamidobenzylic boronate inversion; bipyridine ligand; carbon stereocenters; copper; enantiospecificity; stereospecific reaction.

Nonracemic α-(bromobenzamido)benzylic boronates such as I (R = Me, n-Pr, PhCH2CH2) and ent-I (R = H) underwent stereospecific intramol. Suzuki coupling reactions in the presence of CuCl2 and 2,2′-bipyridine or 6-phenyl-2,2′-bipyridine and mediated by Cs2CO3 and H2O (and in some cases phenol) in toluene/chloroform to yield nonracemic isoindolinones such as II (R = Me, n-Pr, PhCH2CH2) and ent-II (R = H) with inversion of boronate stereochem.

Angewandte Chemie, International Edition published new progress about Cyclization catalysts, stereoselective. 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