Category: 343338-28-3

Cicco, Luciana published the artcileAddition of Highly Polarized Organometallic Compounds to N-tert-Butanesulfinyl Imines in Deep Eutectic Solvents under Air: Preparation of Chiral Amines of Pharmaceutical Interest, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is primary amine preparation enantioselective; sulfinamide preparation chemoselective; sulfinyl imine organometallic compound nucleophilic addition; Grignard reagents; amines; deep eutectic solvents; imines; organolithium reagents.

Chiral N-tert-butanesulfinyl imines (CH3)3S(O)N=CHR (R = Ph, tert-Bu, benzyl, naphthalen-1-yl, etc.) are added smoothly to highly polarized organometallic compounds R1X (X = Li, MgCl; R1 = Me, Bu, prop-2-en-1-yl, Ph, etc.) of s-block elements in the biodegradable D-sorbitol/choline chloride eutectic mixture, thereby granting access to enantioenriched primary amines RCH(NH2)R1 after quant. removing the sulfinyl group. The practicality of the method is further highlighted by proceeding at ambient temperature and under air, with very short reaction times (2 min), enabling the preparation of diastereoisomeric sulfinamides R(R1)CHNHS(O)(CH3)3 in very good yields (74-98%) and with a broad substrate scope, and the possibility of scaling up the process. The method is demonstrated in the asym. syntheses of both the chiral amine side-chain of (R,R)-Formoterol (96% ee) and the pharmaceutically relevant (R)-Cinacalcet (98% ee).

ChemSusChem 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, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide.

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

Weigel, William K. published the artcileSynthesis of amino-diamondoid pharmacophores via photocatalytic C-H aminoalkylation, HPLC of Formula: 343338-28-3, the main research area is amino diamondoid pharmacophore preparation; adamantane imine aminoalkylation photocatalyzed iridium; saxagliptin core rimantadine diastereoselective enantioselective preparation.

A direct C-H aminoalkylation reaction using two light-activated H-atom transfer catalyst systems that enabled the introduction of protected amines to native adamantane scaffolds with C-C bond formation was reported. The scope of adamantane and imine reaction partners was broad and deprotection provided versatile amine and amino acid building blocks. Using readily available chiral imines, the diastereo- and enantioselective synthesis of the saxagliptin core and rimantadine derivatives was also described.

Chemical Communications (Cambridge, United Kingdom) published new progress about Aldimines 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, HPLC of Formula: 343338-28-3.

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

Saraiva Rosa, Nathalie published the artcileEnantiopure β3-Trifluoromethyl-β3-homoalanine derivatives: Coupling with Boc-protected amino acids and conformational studies of peptides in solid state, Recommanded Product: (S)-2-Methylpropane-2-sulfinamide, the main research area is amino acid trifluoromethyl methyl enantioselective synthesis tertbutoxycarbonyl protection; peptide coupling conformation hydrogen bond stability crystal structure.

The use of enantiopure β3-trifluoromethyl-β3-alkyl β-amino acids for the design of peptides would contribute to drastically enhance peptide stability in vivo. Moreover, the steric hindrance generated by the substituents on the tetrasubstituted carbon adjacent to the nitrogen function coupled to the electron-withdrawing effect of the trifluoromethyl group is more likely to influence the 3D conformation of the peptide. Herein, we describe a short, scalable and robust method to synthesize N- and/or C-protected enantiopure (R)- and (S)-β3-trifluoromethyl-β3-Me β-amino acid derivatives and liquid-phase coupling methods suitable for incorporation of Boc-protected amino acids into short α/β- and β-peptides. Conformational studies of some of these original peptides via X-ray diffraction anal. highlighted intraresidue C6 hydrogen bonds within trifluoromethylated amino acids.

Synthesis published new progress about Conformation. 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

Metternich, Jan B. published the artcileAsymmetric Nazarov Cyclizations of Unactivated Dienones by Hydrogen-Bond-Donor/Lewis Acid Co-Catalyzed, Enantioselective Proton-Transfer, Application In Synthesis of 343338-28-3, the main research area is pentadienone Lewis acid catalyst enantioselective Nazarov cyclization; cyclopentenone preparation; Lewis acid; Nazarov; catalysis; electrocyclization; enantioselective; physical organic.

Enantioselective Nazarov cyclization catalyzed by chiral hydrogen-bond-donors in concert with silyl Lewis acids was reported. The developed transformation provides access to tri-substituted cyclopentenones in high levels of enantioselectivity (up to 95% e.e.) from a variety of simple unactivated dienones. Kinetic and mechanistic studies are consistent with a reversible 4π-electrocyclization C-C bond-forming step followed by rate- and enantio-determining proton-transfer as the mode of catalysis.

Advanced Synthesis & Catalysis published new progress about Alkadienones 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 In Synthesis of 343338-28-3.

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

Liu, Jianjian published the artcileChalcogen bond-guided conformational isomerization enables catalytic dynamic kinetic resolution of sulfoxides, Related Products of amides-buliding-blocks, the main research area is chiral sulfoxide preparation enantioselective regioselective; sulfinyl dibenzaldehyde alc esterification.

Conformational isomerization can be guided by weak interactions such as chalcogen bonding (ChB) interactions. Here authors report a catalytic strategy for asym. access to chiral sulfoxides by employing conformational isomerization and chalcogen bonding interactions. The reaction involves a sulfoxide bearing two aldehyde moieties as the substrate that, according to structural anal. and DFT calculations, exists as a racemic mixture due to the presence of an intramol. chalcogen bond. This chalcogen bond formed between aldehyde (oxygen atom) and sulfoxide (sulfur atom), induces a conformational locking effect, thus making the sym. sulfoxide as a racemate. In the presence of N-heterocyclic carbene (NHC) as catalyst, the aldehyde moiety activated by the chalcogen bond selectively reacts with an alc. to afford the corresponding chiral sulfoxide products with excellent optical purities. This reaction involves a dynamic kinetic resolution (DKR) process enabled by conformational locking and facile isomerization by chalcogen bonding interactions.

Nature Communications published new progress about Alcohols 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

Zhu, Bo-Han published the artcileHighly Site-Selective Oxidative Cyclization of Ene-ynamides via Non-Noble-Metal Catalysis: Access to Functionalized Lactams, Category: amides-buliding-blocks, the main research area is lactam preparation diastereoselective regioselective mechanism; chiral lactam preparation diastereoselective regioselective enantioselective mechanism; ene ynamide tandem oxidative cyclization non noble metal catalyst.

Herein, an unprecedented non-noble-metal-catalyzed oxidation/cyclization of ene-ynamides, e.g., R1CCN(R)CH(R2)C(R3):C(Me)R4 (R = Ms, Ts, Bs, benzenesulfonyl; R1 = Ph, 4-chlorophenyl, thiophen-2- yl, etc.; R2 = H, Et, allyl, prop-2-yn-1-yl; R3 = H, Me; R4 = Me, Ph), is developed, allowing the synthesis of diversely functionalized lactams, e.g., I and II, in moderate to good yields with excellent diastereoselectivities without the observation of typical cyclopropanation products. In combination with Ellman′s tert-butylsulfinimine chem., chiral γ-lactams containing three contiguous stereocenters are obtained with high diastereo- and enantioselectivity. Moreover, d. functional theory (DFT) calculations indicate that this protocol probably undergoes a carbon cation or proton transfer process.

Organic Letters published new progress about Alkynes 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, Category: amides-buliding-blocks.

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

Liang, Hao published the artcileChiral Arene Ligand as Stereocontroller for Asymmetric C-H Activation, SDS of cas: 343338-28-3, the main research area is chiral arene ruthenium ligand preparation; isoquinolone preparation regioselective enantioselective; amide alkyne carbon hydrogen activation; Asymmetric C−H Activation; Axially Chiral; Chiral Arene Ligand; Ruthenium; [2.2]Paracyclophane.

Development of chiral ligands is the most fundamental task in metal-catalyzed asym. synthesis. In the last 60 years, various kinds of ligands have been sophisticatedly developed. However, it remains a long-standing challenge to develop practically useful chiral η6-arene ligands, thereby seriously hampering the asym. synthesis promoted by arene-metal catalysts. Herein, the design and synthesis of a class of readily tunable, C2-sym. chiral arene ligands derived from [2.2]paracyclophane is reported. Its ruthenium(II) complexes have been prepared and successfully applied in the enantioselective C-H activation to afford a series of axially chiral isoquinolones (up to 99% yield and 96% ee). This study not only lays chemists’ longstanding doubts about whether it is possible to use chiral arene ligands to stereocontrol ruthenium(II)-catalyzed asym. C-H activation, but also opens up a new avenue to achieve asym. C-H activation.

Angewandte Chemie, International Edition published new progress about Amides 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, SDS of cas: 343338-28-3.

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

Salah, Kennouche published the artcileStereoselective Synthesis of Biheterocycles Containing Indole and 5,6-Dihydropyridin-2(1H)-one or α-methylene-β-butyrolactam Scaffolds, Application of (S)-2-Methylpropane-2-sulfinamide, the main research area is biheterocycle containing indole preparation; dihydropyridinone preparation; alpha methylene beta butyrolactam scaffold preparation.

Indium-mediated allylation of N-tert-butanesulfinyl imines derived from indole-2 and 3-carbaldehydes I [R1 = H, Me, Et; R2 = H, 4-Br, 5-OMe, etc.] and II with allylic bromides, proceed with high diastereoselectivity. Homoallylic amide derivatives were transformed into dihydropyridinones, e.g., III and IV, upon successive desulfinylation, N-acylation with acryloyl chloride and ring-closing-metathesis. Desulfinylation of amine ester derivatives obtained when Et 2-(bromomethyl)acrylate was used as the allylating reagent, led to the corresponding α-methylene-β-butyrolactams in modest yields.

ChemistrySelect published new progress about Lactams 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

Zhang, Minxuan published the artcileK3PO4-Promoted domino reactions: diastereoselective synthesis of trans-2,3-dihydrobenzofurans from salicyl N-tert-butanesulfinyl imines and sulfur ylides, Product Details of C4H11NOS, the main research area is trans dihydrobenzofuran preparation chemoselective enantioselective diastereoselective; salicyl tert butylsulfinyl imine preparation sulfur ylide domino annulation.

An efficient domino annulation between sulfur ylides and salicyl N-tert-butylsulfinyl imines was developed. The reaction proceeded with a diastereodivergent process, the configuration of the sulfinyl group determining the stereochem. course of the reaction. The method allowed the synthesis of a highly substituted trans-2,3-dihydrobenzofuran skeletons I [R1 = H, 4-Cl, 4-Me, 4-NO2; R2 = H; R3 = H, Cl, Br; R4 = H, Cl; R2R3 = CH:CC:CH] with high yield and good chemo- and diastereoselectivity.

RSC Advances 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, Product Details of C4H11NOS.

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

Kodama, Yuki published the artcileStereoselective synthesis of highly functionalized (Z)-chloroalkene dipeptide isostere containing an α,α-disubstituted amino acid, Safety of (S)-2-Methylpropane-2-sulfinamide, the main research area is chloroalkene dipeptide isostere enantioselective diastereoselective synthesis disubstituted amino acid; ketimine Aza Darzens condensation dichloroenolate aldimine; cyclization mechanism transition state free energy NBO DFT; quaternary carbon center spirocyclic crystal mol structure packing.

Described here is the first stereoselective synthesis of highly functionalized chloroalkene dipeptide isosteres containing an α,α-disubstituted amino acid (ααAA). This synthesis requires the construction of a quaternary carbon center, and this challenge was overcome by the Aza-Darzens condensation of ketimine with α,α-dichloroenolate, producing 2-chloroaziridines with quaternary carbon centers including spirocyclic motifs, which are valuable for the previously elusive synthesis of various α,α-AA-containing chloroalkene isosteres.

Chemical Communications (Cambridge, United Kingdom) published new progress about Amino acids Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (disubstituted). 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