Category: 343338-28-3

O’Mahony, Donogh J. R. published the artcileA practical asymmetric synthesis of ortho-substituted 4-pyrazolyl-2-ethylamines, Formula: C4H11NOS, the main research area is pyrazolyl ethylamine preparation enantioselective.

A reliable three-step synthesis of ortho-substituted 4-pyrazolyl-2-ethylamines, e.g., I, starting from a pyrazole Me ketone, e.g., 1-{5-[(benzyloxy)methyl]pyrazolo[1,5-a]pyridin-3-yl}ethan-1-one, and N-tert-butanesulfinylamine is described. Strongly dehydrating conditions were required to form the N-tert-butanesulfinyl ketimines, but these intermediates were stable to aqueous work-up and chromatog. Reduction of N-tert-butanesulfinyl ketimines with L-selectride, or Super-hydride, in THF afforded excellent yields and diastereoselectivities of the sulfinamides II, which were converted into chiral amines with methanolic HCl. The 4-pyrazolyl-2-ethylamines resulted from these investigations are attractive building blocks for medicinal chemists, as they exhibit low mol. weight, and low calculated octanol-water partition coefficient (c Log P values), while disrupting planarity with three-dimensional character. For example, the amine products were utilized in structure-activity studies of the human transient receptor potential vanilloid 1 (TRPV1/VR1).

Tetrahedron Letters published new progress about Alkyl aryl ketones 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, Formula: C4H11NOS.

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

Wang, Huamin published the artcileCatalytic Enantiodivergent Michael Addition by Subtle Adjustment of Achiral Amino Moiety of Dipeptide Phosphines, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is chiral alkylpyridazinone preparation enantioselective; pyridazinone enone hydroamination Michal addition chiral dipeptide phosphine catalyst; Chemistry; Organic Chemistry; Organic Chemistry Methods.

Inspired by the biol. system, an unprecedented catalytic enantiodivergent Michael addition of pyridazinones I (R = H, 5-Cl, 6-Ph, 4,5-Br2, etc.) to enones R1C(O)CH:CHR2 (R1 = 4-chlorophenyl, naphthalen-2-yl, 1-benzothiophen-2-yl, etc.; R2 = CF3, C2F5, C(O)OEt, etc.) by subtle adjustment of achiral amino moiety of dipeptide phosphine catalysts II (R3 = Ph, 3,5-di-tert-butylphenyl; R4 = [3,5-bis(trifluoromethyl)phenyl]carbonyl, (2S)-2-([(tert-butoxy)carbonyl]amino)-3-methylbutanyl, 2-methylpropane-2-sulfinyl, etc.) was reported. These two dipeptide phosphine catalysts, II (R3 = phenyl; R4 = (2S)-2-([(tert-butoxy)carbonyl]amino)-3-methylbutanoyl; R3 = phenyl; R4 = (2S)-2-[(3,5-dinitrophenyl)formamido]-3-methylbutanoyl) could deliver both enantiomers of a series of N2-alkylpyridazinones S/R-III in good yields (up to 99%) with high enantioselectivities (up to 99% ee) via the catalyst-controlled enantiodivergent addition of pyridazinones I to enones R1C(O)CH:CHR2.

iScience published new progress about Dipeptides, phosphono analogs Role: CAT (Catalyst Use), USES (Uses). 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

Gohari, Seyed Jamaladdin published the artcileNovel enantioselective synthesis of (S)-ketamine using chiral auxiliary and precursor Mannich base, Synthetic Route of 343338-28-3, the main research area is chlorophenyl methylamino cyclohexanone enantioselective preparation.

Chiral auxiliaries such as tert-butanesulfinamide (TBSA) was used for the asym. synthesis of (S)-ketamine. Condensation of TBSA with ketones provides corresponding tert-butanesulfinylimine in consistently high yields. The tert-butanesulfinyl group actuates the imine for nucleophilic addition, is a potent chiral directing group, and after nucleophilic addition is easily dissociated by intervention with acid solution A Mannich base, 2-(N-piperidinomethyl)-1-phenylcyclohexylamine was synthesized via Mannich reaction starting from cyclohexanone. Then, corresponding sulfiniylimine was obtained by the condensation of TBSA with formed aminoketone. By using salts such as Ti(OEt)4, N-tert-butanesulfinylketimine was obtained in 85% yield. Next, a new chiral center was generated using Grignard reagent as nucleophile at -78° (80% yield). Finally, after many steps, the (S)-ketamine was synthesized under ozonolysis conditions with good yield and enantioselectivity (75% yield and 75% ee).

Canadian Journal of Chemistry published new progress about Amines, keto 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, Synthetic Route of 343338-28-3.

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

Kwiatkowska, Magdalena published the artcileThe self-disproportionation of enantiomers (SDE) via column chromatography of β-amino-α,α-difluorophosphonic acid derivatives, COA of Formula: C4H11NOS, the main research area is aminophosphonic acid ester synthesis self disproportionation enantiomer column chromatog; acetylated benzyloxycarbonyl dipeptide amine SDEvC aminophosphonic acid; hydrogen bond dimer chirality; Achiral chromatography; Amino acids and derivatives; Enantioenrichment/-depletion; Molecular chirality; Self-disproportionation of enantiomers (SDE).

This work presents the first study of the self-disproportionation of enantiomers via chromatog. (SDEvC) of β-aminophosphonic acid esters, several of which have been synthesized for the first time. Three types of structures were examined, N-acetylated, dipeptide construction with N-Cbz (Cbz = benzyloxycarbonyl) glycine, and a free amine. In the latter case, this is the first time that SDEvC has been reported for free amine amino acids. In all the three types of structures, significant SDE magnitudes (Δee’s up to 55%) were exhibited underscoring the ubiquitous nature of the SDE phenomenon. Chem. models of homo- vs. heterochiral intermol. interactions are proposed to rationalize the SDE magnitude differences amongst these new β-aminophosphonic acid derivatives In addition, the incorporation of addnl., competing binding modes to a mol., was found to lead to a reduction of the SDE magnitude by shifting the intermol. binding away from the stereogenic center and/or by leading to a convoluted binding system that disrupts the structured and relatively stable assemblies that give rise to the SDE.

Amino Acids published new progress about Acid chlorides 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

Ma, Peng-Ju published the artcileAddition-Rearrangement of Ketenes with Lithium N-tert-Butanesulfinamides: Enantioselective Synthesis of α,α-Disubstituted α-Hydroxycarboxylic Acid Derivatives, Synthetic Route of 343338-28-3, the main research area is hydroxycarboxamide enantioselective preparation; nonracemic sulfonamide lithiation stereoselective addition ketene rearrangement; tandem stereoselective addition sulfinamide ketene rearrangement.

Addition of the lithium salts of nonracemic sulfinamides such as I (generated in situ) to ketenes such as PhEtC:C:O (either prepared or generated in situ from the corresponding acyl chlorides) followed by Mislow-Evans [2,3]-sigmatropic rearrangement yielded sulfenates of α-hydroxycarboxamides such as II; the absolute stereochem. of the sulfinamide was transferred to the new stereocenter with high fidelity.

Organic Letters published new progress about Acid chlorides 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

Shen, Xianfu published the artcileCopper(I)-Catalyzed Cascade Cyclization to the Total Synthesis of Hexahydropyrroloindole Alkaloids: Flustramine B and Debromoflustramine B, Safety of (S)-2-Methylpropane-2-sulfinamide, the main research area is oxindole copper catalyst cascade cyclization one pot; hexahydropyrroleindole alkaloid preparation.

The total synthesis of two bioactive hexahydropyrroloindole (HPI) alkaloids beared a C3a tetrasubstituted stereocenters substituted by isopentenyl. This route was based on Cu-catalyzed cascade arylation-alkylation sequence in one-pot as a key step, provided Flustramine B and Debromoflustramine B with 9 steps in 37.6% and 31.1% overall yields, resp.

ChemistrySelect published new progress about Alkaloids 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, Safety of (S)-2-Methylpropane-2-sulfinamide.

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

Chen, Wen published the artcileStructure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids, Product Details of C4H11NOS, the main research area is sarpagine ajmaline koumine alkaloid preparation.

A unified approach towards the asym. synthesis of three types of alkaloids, leading to a collective synthesis of 14 natural alkaloids is reported. Among them, akuammidine, 19-Z-akuammidine, vincamedine, vincarine, quebrachidine, vincamajine, alstiphyllanine J, and dihydrokoumine were accomplished for the first time. Features of this synthesis are a new Mannich-type cyclization to construct the key indole-fused azabicyclo[3.3.1]nonane common intermediate, an SmI2-mediated coupling to fuse the aza-bridged E-ring, stereoselective olefinations to install either the 19-E or 19-Z terminal alkenes presented in the natural alkaloids, and an efficient iodo-induced cyclization to establish the two vicinal all-carbon quaternary centers in the koumine-type alkaloids.

Nature Communications published new progress about Alkaloids 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, Product Details of C4H11NOS.

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

Dawood, Rafid S. published the artcileStereodivergent Total Syntheses of (+)-Monomorine I and (+)-Indolizidine 195B, Formula: C4H11NOS, the main research area is indolizidine alkaloid preparation diastereoselective enantioselective; monomorine alkaloid preparation diastereoselective enantioselective.

A simple and efficient stereoselective total synthesis of two natural products (+)-monomorine I and (+)-indolizidine 195B in high yields starting from a readily available alc. is described. The key step in this synthetic route exploits the judicious use of solvent to enable a closed or open transition state in a nucleophilic addition of Grignard reagent to sulfinimine, giving selective access to two distinct diastereomers required for the formation of the two target natural products.

European Journal of Organic Chemistry published new progress about Alkaloids 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, Formula: C4H11NOS.

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

Jin, Ming Yu published the artcileSimultaneous Kinetic Resolution and Asymmetric Induction within a Borrowing Hydrogen Cascade Mediated by a Single Catalyst, Category: amides-buliding-blocks, the main research area is unsaturated ketone preparation; alkoxy ketone preparation; ketone amino preparation; alc alkoxy preparation enantioselective; amino alc preparation enantioselective; racemic allylic alc borrowing hydrogen cascade ruthenium catalyst; asymmetric induction; borrowing hydrogen cascade; density functional theory; kinetic resolution; π-π interactions.

In a borrowing hydrogen cascade starting from racemic allylic alcs., one of the enantiomers could be kinetically resolved, while the other enantiomer could be purposely converted to various targeted products, including α,β-unsaturated ketones RC(O)C=CCH2R1 [R = Ph, 4-FC6H4, 2-naphthyl, etc.; R1 = (CH2)6, (CH2)7, OTBS], β-functionalized ketones R2C(O)CH2CH2R3 [R2 = 4-MeSC6H4, 4-t-BuC6H4, 4-MeOC6H4, etc.; R3 = OMe, OEt, morpholino, etc.] and γ-functionalized alcs. R4CH(OH)CH2CH2R5 [R4 = 4-ClC6H4, 4-FC6H4, 2-naphthyl, etc.; R5 = OMe, OBn, morpholino, etc.] was reported. By employing a robust Ru-catalyst, both kinetic resolution and asym. induction were achieved with remarkable levels of efficiency and enantioselectivity. D. functional theory (DFT) calculations suggested that corresponding catalyst-substrate π-π interactions were pivotal to realize the observed stereochem. diversity.

Angewandte Chemie, International Edition published new progress about Alcohols, alkoxy 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, Category: amides-buliding-blocks.

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

Ramaiah, Manjunatha M. published the artcile1,8-Diazabicyclo[5.4.0]undec-7-ene-mediated formation of N-sulfinyl imines, Application of (S)-2-Methylpropane-2-sulfinamide, the main research area is sulfinyl imine preparation; tert butanesulfinamide aldehyde para toluenesulfinamide condensation DBU mediated; para toluenesulfinamide alc tert butanesulfinamide condensation DBU mediated.

A facile and efficient method was developed for the preparation of a variety of aryl, heteroaryl, and alkyl N-sulfinyl imines RCH=NS(O)R1 [R = cyclopropyl, 2-FC6H4, 8-quinolinyl, etc.; R1 = tBu, 4-MeC6H4; stereo = (S)] using 1,8-diazabicyclo[5.4.0]undec-7-ene. In addition to tert-butanesulfinamide, the condensation was also effective with p-toluenesulfinamide. The reaction was performed at room temperature and produced corresponding N-sulfinyl imines RCH=NS(O)R1 in excellent yields in absence of acids, metals, and additives. This methodol. was also useful for the preparation of N-sulfinyl imines on gram scale. A one-pot synthesis was developed using aryl and heteroaryl alcs. with both tert-butanesulfinamide and p-toluenesulfinamide at room temperature, resulting in corresponding N-sulfinyl imines with good yields.

Journal of Chemical Research published new progress about Alcohols, unsaturated 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