119461-40-4

Usage

Uses

Used in Organic Synthesis:
(S)-1-Tosyl-2-methylaziridine is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure and reactivity make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. (S)-1-Tosyl-2-methylaziridine's chirality and stability contribute to its utility in creating enantioselective products, which are essential in many biologically active molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-1-Tosyl-2-methylaziridine is used as a key intermediate in the synthesis of chiral drugs. Its specific stereochemistry allows for the development of enantiomerically pure compounds, which is critical for ensuring the desired biological activity and minimizing potential side effects. (S)-1-Tosyl-2-methylaziridine's role in drug synthesis can lead to the creation of new medications with improved efficacy and safety profiles.
Used in Research and Development:
(S)-1-Tosyl-2-methylaziridine is also utilized in academic and industrial research settings for the exploration of new synthetic methods and the development of innovative chemical processes. Its unique properties make it an interesting subject for studying reaction mechanisms, catalysts, and other aspects of organic chemistry. Additionally, it can be used to test and validate new synthetic strategies and techniques in the field of asymmetric synthesis.

InChI:InChI=1/C10H13NO2S/c1-8-3-5-10(6-4-8)14(12,13)11-7-9(11)2/h3-6,9H,7H2,1-2H3/t9-,11?/m0/s1

Upstream product

• 88129-44-6 (S)-N-(p-toluenesulfonyl)-2-amino-1-propyl p-toluenesulfonate 
• 56-41-7 L-alanin 
• 98-59-9 p-toluenesulfonyl chloride 
• 59724-69-5 (S)-N-tosylalanine methyl ester 
• 4816-81-3 p-tosyl-L-alanine 
• 100132-60-3 (S)-2-(toluene-4-sulfonamido)propan-1-ol 
• 2749-11-3 (S)-Alaninol 

Downstream Products

• 119461-41-5 (S)-N-(p-toluenesulfonyl)-4-amino-1-(trimethylsilyl)-1-pentyne 
• 196520-91-9 N(CH₂CH(Me)NH(4-CH₃(C₆H₄)SO₂))3 
• 362495-77-0 [2S,4S,1'S,2'S]-(+)-N,2-dimethyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4-(p-toluenesulfonylamino)pentanamide 
• 406937-95-9 N-[(1S)-2-(1-benzothien-3-yl)-1-methylethyl]-4-methylbenzenesulfonamide 
• 34542-12-6 4-methyl-N-[(1S)-1-methyl-2-phenylethyl]benzenesulfonamide 
• 406937-96-0 4-methyl-N-[(1S)-1-methyl-2-(1-naphthyl)ethyl]benzenesulfonamide 
• 1027839-81-1 C₂₃H₃₆N₄O₄S₂ 
• 460743-46-8 N-[(1S)-2-(benzylamino)-1-methylethyl]-4-methylbenzenesulfonamide 
• 460743-51-5 N-{(1S)-2-[benzyl((2S)-{[(4-methylphenyl)sulfonyl]amino}propyl)amino]-1-methylethyl}-4-methylbenzenesulfonamide 
• 462119-78-4 4-methyl-N-{(1S)-1-methyl-2-[((2S)-2-{[(4-methylphenyl)sulfonyl]amino}propyl)amino]ethyl}benzenesulfonamide 
• 670069-56-4 [(1S)-2-amino-1-methylethyl]-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

A general method for the preparation of chiral TREN derivatives

A general procedure for the preparation of C3-symmetric TREN derivatives with backbone chirality has been developed. Stereo- and regioselective ring opening by ammonia of (S)-N-tosyl-2-isopropylaziridine, obtained starting from either the corre

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.

Synthesis of Enantiopure PZM21: A Biased Agonist of the Mu-Opioid Receptor

PZM21 (1) was recently reported as a biased agonist of the mu-opioid receptor (MOR) with improved antinociceptive effects and reduced side effects compared with traditional opioid-based analgesics. The original synthesis of PZM21 with the desired (S,S) configuration required the separation of a diastereomeric mixture in the final step by using chiral HPLC. A concise synthesis of 1 has now been developed in the enantiomeric pure form starting with commercially available l-alanine and proceeding via a chiral aziridine as a key intermediate. The final product was obtained as the (S,S) diastereomer in seven steps in 22.5 % yield from l-alanine. This synthetic strategy could be readily applied to the development of PZM21 analogues at the thiophenyl position.

Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy

Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.

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.

A Modular Synthesis of Multidentate S-, N- and O-Containing Meta- and Paracyclophanes

The development of a modular approach to macrocycle assembly has enabled the synthesis of a library of pyridine-based macrocycles possessing multiple donor sites where chirality was readily introduced from (R)- or (S)-alanine, a representative amino acid. The facile, regioselective, nucleophilic ring opening of aziridines by dithiols enabled the synthesis of thioether-based linkers which on subsequent alkylation provided access to optically pure macrocycles. A modular approach to macrocyclic assembly has enabled the synthesis of a library of macrocycles possessing multiple donor sites where chirality was readily introduced from (S)-alanine. Key to this approach was the facile, regioselective, nucleophilic ring opening of aziridines by dithiols followed by macrocylisation under conditions of high dilution.

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