124575-31-1

Upstream product

• 7533-40-6 (S)-2-amino-4-methylpentan-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 7517-19-3 methyl (L)-leucinate hydrochloride 
• 51220-84-9 (S)-methyl 4-methyl-2-(4-methylphenylsulfonamido)pentanoate 
• 61-90-5 L-leucine 
• 1220-80-0 (S)-4-methyl-2-(toluene-4-sulfonamido)pentanoic acid 
• 130748-67-3 (2S)-N-(4-methylbenzene)-1-sulfonoamido-4-methylpentan-1-ol 
• 203871-42-5 (S)-2-(diphenylphosphinamido)-4-methylpentan-1-ol 

Downstream Products

• 406937-93-7 (S)-4-methyl-N-(4-methyl-1-phenylpentan-2-yl)benzenesulfonamide 
• 934472-27-2 (R)-N-(para-toluenesulfonyl)-(1-isobutyl-4-pentenyl)amine 
• 1269526-71-7 (S)-4-methyl-N-(4-methyl-1-(phenylselanyl)pentan-2-yl)benzenesulfonamide 
• 925425-86-1 N,N′-[(2S,2′S)-diselanylbis(4-methylpentane-2,1-diyl)]bis-(4-methylbenzenesulfonamide) 
• 884639-59-2 (S)-1-isobutyl-5-(tetrahydropyran-2-yloxy)-N-toluenesulfonyl-pent-3-ynylamine 
• 406937-91-5 N-[(1S)-1-(1-benzothien-3-ylmethyl)-3-methylbutyl]-4-methylbenzenesulfonamide 
• 406937-90-4 4-methyl-N-[(1S)-3-methyl-1-(3-thienylmethyl)butyl]benzenesulfonamide 
• 203207-82-3 N-[(S)-1-Isobutyl-5,5-dimethoxy-3-(toluene-4-sulfonyl)-pentyl]-4-methyl-benzenesulfonamide 
• 154047-42-4 (S)-1-(2-trimethylsilyl-1,3-dithian-2-yl)-2-(4-methylbenzenesulfonamido)-4-methylpentane 
• 154047-38-8 (S)-1-(2-methyl-1,3-dithian-2-yl)-2-(4-methylbenzenesulfonamido)-4-methylpentane 
• 154047-36-6 (S)-1-(1,3-dithian-2-yl)-2-(4-methylbenzenesulfonamido)-4-methylpentane 
• 1258948-42-3 (3RS,5S)-3-ethoxycarbonyl-5-(2-methylpropyl)-1-toluene-p-sulphonylpyrrolidin-2-one 

Relevant academic research and scientific papers

Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines

Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.

Cu-Catalyzed [3 + 3] Cycloaddition of Isocyanoacetates with Aziridines and Stereoselective Access to α,γ-Diamino Acids

We report herein an efficient Cu-catalyzed formal [3 + 3] cycloaddition of isocyanoacetates with readily available aziridines of different substitution patterns, which provides a practical access to valuable 1,4,5,6-tetrahydropyrimidine derivatives. In pa

Enantiodivergent Synthesis of (+)- and (?)-Pyrrolidine 197B: Synthesis of trans-2,5-Disubstituted Pyrrolidines by Intramolecular Hydroamination

A highly efficient, diastereoselective, iron(III)-catalyzed intramolecular hydroamination/cyclization reaction involving α-substituted amino alkenes is described. Thus, enantiopure trans-2,5-disubstituted pyrrolidines and trans-5-substituted proline derivatives were synthesized by means of a combination of enantiopure starting materials, easily available from l-α-amino acids, with sustainable metal catalysts such as iron(III) salts. The scope of this methodology is highlighted in an enantiodivergent approach to the synthesis of both (+)- and (?)-pyrrolidine 197B alkaloids from l-glutamic acid. In addition, a computational study was carried out to gain insight into the complete diastereoselectivity of the transformation.

Metal-free one-pot synthesis of 2-substituted and 2,3-disubstituted morpholines from aziridines

The metal-free synthesis of 2-substituted and 2,3-disubstituted morpholines through a one-pot strategy is described. A simple and inexpensive ammonium persulfate salt enables the reaction of aziridines with halogenated alcohols to proceed via an SN2-type ring opening followed by cyclization of the resulting haloalkoxy amine.

An efficient synthetic approach for N-C bond formation from (S)-amino acids: An easy access to cis-2,5-disubstituted chiral piperazines

An efficient synthetic strategy is described for the construction of amino acids derived enantiomerically pure cis-2,5-disubstituted chiral piperazines. Cu-catalyzed spontaneous regioselective ring opening and ring closing of non-activated N-tosyl aziridines as well as Pd-mediated N-C bond formation from N-tosyl halogenated amino-derivatives are the key steps for accessing disubstituted piperazines.

Fluoroalkanosulfonyl fluorides-mediated cyclodehydration of β-hydroxy sulfonamides and β-hydroxy thioamides to the corresponding aziridines and thiazolines

An efficient method for the fluoroalkanosulfonyl fluoride-induced cyclodehydration of β-hydroxy sulfonamides and β-hydroxy thioamides to the corresponding aziridines and thiazolines is reported. Mild reaction conditions, operational simplicity, and high y

Regioselective ring-opening of amino acid-derived chiral aziridines: An easy access to cis-2,5-disubstituted chiral piperazines

An efficient four-step synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino-acid-based aziridines is described. The key steps in this strategy are the highly regioselective boron trifluoride diethyl etherate (BF3·OEt2)-mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochloride followed by Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. The pied piperazines: A four-step efficient synthetic strategy for cis-2,5-disubstituted chiral piperazines derived from amino acid-based aziridines is described. The key reaction steps are the highly regioselective BF3·OEt2 mediated ring-opening of less-reactive N-Ts chiral aziridines by α-amino acid methyl ester hydrochlorides, followed by a Mitsunobu cyclization. This protocol has been used in an attempt to construct the piperazine core framework of natural product (+)-piperazinomycin. Copyright

One-pot and microwave-assisted synthesis of N-sulfonylaziridines

A novel and efficient microwave-assisted one-step reaction was developed to synthesize chiral N-sulfonylaziridines by the reaction of different chiral amino alcohols and sulfonic chlorides. The newly developed microwave synthetic method has the advantage of reducing the reaction time from 24 to 0.5 h with improved yields (84-93%) and minimizing by-products.

Development of biisoquinoline-based chiral diaminocarbene ligands: Enantioselective SN2′ allylic alkylation catalyzed by copper-carbene complexes

Chiral biisoquinoline-based diaminocarbene ligands (BIQ) were designed to create a chiral environment extended toward the metal center, which was confirmed by an X-ray structure. The concise ligand synthesis is highlighted by a modified Bischler-Napieralski cyclization of bisamides prepared from readily available chiral phenethylamines, and allows easy variation of the stereodifferentiating groups. The cyclohexyl-BIQ-copper complex is an efficient catalyst for enantioselective SN2′ allylic alkylation with Grignard reagents showing SN2′ regioselectivity higher than 5:1 and enantioselectivity in the range of 68-77% ee.

Large scale synthesis of optically pure aziridines

Disclosed is an efficient, inexpensive method for the preparation of chiral aziridines on a large scale.