1605-06-7

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3S)-2,3-diphenylaziridine serves as a crucial building block in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity allow for the creation of complex organic molecules that can be utilized in the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, (2R,3S)-2,3-diphenylaziridine is employed as a key intermediate in the production of pesticides and other agrochemicals. Its versatility in organic synthesis contributes to the development of effective and targeted pest control solutions.
Used in Organic Synthesis:
(2R,3S)-2,3-diphenylaziridine is used as a synthetic building block for the preparation of a wide range of organic compounds. Its specific stereochemistry and reactivity enable the synthesis of complex molecules with potential applications in various fields, including materials science, medicinal chemistry, and specialty chemicals.

Upstream product

• 13698-13-0 Ethyl N-(2-chloro-1,2-diphenylethyl)carbamate 
• 53986-95-1 N-(α-trimethylsilylbenzyl)benzylideneamine 
• 91666-83-0 1,2-diphenyl-1-(4,5-diphenyl-2H-1,2,3-triazol-2-yl)-2H-azirine 
• 49855-40-5 L_g-threo-α'-chloro-bibenzyl-α-ylamine 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 957188-81-7 cis-2,3-diphenyl-N-[(trifluoromethyl)sulfonyl]aziridine 
• 645-49-8 cis-stilben 
• 1151538-49-6 trans-(2S,3S)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(R)-(p-toluenesulfinyl)]aziridine 
• 52340-78-0 (R,R)-hydroxybenzoin 
• 183184-04-5 (R,R)-(+)-4,5-diphenyl-1,3,2-dioxathiolan-2-one 
• 23190-16-1 (1R,2S)-2-Amino-1,2-diphenylethanol 
• 49855-40-5 D-erythro-α'-chloro-bibenzylyl-(α)-amine 
• 133522-22-2 (1R,2S)-2-azido-1,2-diphenylethan-1-ol 
• 1689-71-0 cis-1,2-diphenyloxirane 

Downstream Products

• 530-36-9 erythro-2-amino-1,2-diphenylethanol 
• 530-36-9 threo-1,2-diphenyl-2-aminoethan-1-ol 
• 7042-08-2 cis-1-(4-nitrobenzoyl)-2,3-diphenylaziridine 
• 632-50-8 1,1,2,2-tetraphenylethane 
• 96179-35-0 N-(1,2,2-Triphenylethyl)benzamid 
• 71027-98-0 trans-2,4,5-triphenyl-Δ²-oxazoline 
• 58821-35-5 2,4,5-triphenyl-4,5-dihydrooxazole 
• 645-49-8 cis-stilben 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 37835-64-6 phenyl (2,4,5-triphenyl-1H-pyrrol-3-yl)methanone 
• 98304-59-7 (E)-1-(cis-2,3-diphenylaziridinyl)-1,2-dibenzoylethylene 

Relevant academic research and scientific papers

On the Mechanism of the Aziridine Synthesis from 2-Azido-alcohols and Triphenylphosphine

The reaction of selected 2-azido-alcohols, their pivalates, and methanesulfonates with triphenylphosphine was investigated.It is shown that the formation of aziridines from 2-azido-alcohols proceeds via 1,3,2λ5-oxazaphospholidines.Furthermore, the first synthesis of the unsubstituted acenaphthene-1,2-imine is described.

Chiral sulfide - phosphine ligand and preparation method and use thereof

The present invention provides a novel chiral thioether-phosphine ligand and a preparation method and application thereof. The ligand is a compound shown as a formula I, or enantiomer, non-enantiomer, racemate, pharmaceutically acceptable salt, hydrate and solvate crystal thereof. R1 is an optionally substituted phenyl, and optionally substituted naphthyl; and R2 is methyl and benzyl. The chiral thioether-phosphine ligand provided by the invention as a copper-catalyzed asymmetric cycloaddition ligand can be directly used to prepare various pyrrolidine compounds with substituted multiple chiral centers.

Enantioselective synthesis of tetrahydrofuran derivatives by sequential henry reaction and iodocyclization of γ,δ-unsaturated alcohols

A sequential one-pot Cu-catalyzed asymmetric Henry reaction and iodocyclization is disclosed. The transformation provides efficient access to biologically and synthetically useful 2,2,5-trisubstituted tetrahydrofuran derivatives. The combination of Cu(OAc)2·H2O with a novel chiral sulfoxide-Schiff base hybrid ligand under mild reaction conditions tolerates a wide range of 4-substituted γ,δ-unsaturated aldehydes, and the subsequent iodocyclization furnishes the corresponding products in generally high yields with excellent enantioselectivities. The products can be easily converted into amines with excellent diastereo- and enantioselectivities.

Activation of carboxylic acids in asymmetric organocatalysis

Organocatalysis, catalysis using small organic molecules, has recently evolved into a general approach for asymmetric synthesis, complementing both metal catalysis and biocatalysis.1 Its success relies to a large extent upon the introduction of novel and generic activation modes.2 Remarkably though, while carboxylic acids have been used as catalyst directing groups in supramolecular transition-metal catalysis,3 a general and well-defined activation mode for this useful and abundant substance class is still lacking. Herein we propose the heterodimeric association of carboxylic acids with chiral phosphoric acid catalysts as a new activation principle for organocatalysis. This self-assembly increases both the acidity of the phosphoric acid catalyst and the reactivity of the carboxylic acid. To illustrate this principle, we apply our concept in a general and highly enantioselective catalytic aziridine-opening reaction with carboxylic acids as nucleophiles. Activation by dimerization: There is still no general activation mode for carboxylic acids in organocatalysis. The formation of heterodimers between chiral phosphoric acid diesters and carboxylic acids can be used to activate and direct reactivity of the latter in asymmetric reactions. This novel principle has been applied to the ring-opening desymmetrization and kinetic resolution of aziridines leading to valuable amino alcohols.

Design of chiral sulfoxide-Schiff base hybrids and their application in Cu-catalyzed asymmetric Henry reactions

A new class of chiral sulfoxide-Schiff base ligands has been developed by the rational combination of two privileged chiral backbones. These sulfoxide-Schiff base ligands were found to be highly efficient for Cu-catalyzed asymmetric Henry reactions (up to

Synthesis and structure of hypervalent diacetoxybromobenzene and aziridination of olefins with imino-λ3-bromane generated in situ under metal-free conditions

Ligand exchange of p-CF3C6H4BrF 2 with acetoxy groups using AcOH and Ac2O affords (diacetoxybromo)benzene in a high yield, which undergoes aziridination of alkenes in the presence of TfNH2

2-(p-Tolylsulfinyl)benzyl halides as efficient precursors of optically pure trans-2,3-Disubstituted aziridines

Aziridination of (R)-N-sulfinylaldimines (aryl, heteroaryl and alkenyl derivatives) with 2-(p-tolyl sulfinyl)benzyl iodide in the presence of sodium hexamethyl disilazide takes place with almost complete control of the stereoselectivity (facial and antil

Stereoselective control of planar α-dimethylsulfonium benzyl carbanions. Synthesis of optically pure trans-aziridines

(Chemical Equation Presented) (R)-N-Sulfinylimine and (S)-N-sulfinylimine react with the ylide derived from (S)-dimethyl-[2-(p-toluenesulfinyl) phenyl]sulfonium salt, affording trans-2,3-disubstituted aziridines. A complete trans selectivity in low facial

Bronsted acid-catalyzed desymmetrization of meso-aziridines

The enantioselective ring-opening of meso-aziridines with azide nucleophiles proceeded in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction affords the formation of the products in excellent yield and enantioselectivity. Preliminary mechanistic studies indicate that the active catalytic species is a chiral silane that is generated in situ. Copyright

Aminosulf(ox)ides as Ligands for Iridium(I)-Catalyzed Asymmetric Transfer Hydrogenation

A new class of efficient catalysts was developed for the asymmetric transfer hydrogenation of unsymmetrical ketones. A series of chiral N,S-chelates (6-22) was synthesized to serve as ligands in the iridium(I)-catalyzed reduction of ketones. Both formic a