683226-93-9

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 343338-28-3 (S)-2-methylpropane-2-sulfinamide 

Downstream Products

• 1174267-73-2 1-[(1,1-dimethylethyl)sulfinyl]-2-(4-nitrophenyl)aziridine 

Relevant academic research and scientific papers

Asymmetric Vinylogous Aza-Darzens Approach to Vinyl Aziridines

A new asymmetric approach to assemble cis-vinyl aziridines is reported. A reaction of strategically substituted dienolates, decorated with a γ-leaving group, with chiral sulfinimines afforded chiral vinyl aziridine products in good to excellent yields. This is the first systematic study toward the realization of a useful asymmetric vinylogous aza-Darzens reaction. The reaction is initiated by a syn-selective addition, affording cis-vinyl aziridine products after displacement of bromide. The low syn-diastereoselectivity is attributed to competing retro-Mannich pathways.

Synthesis of enantiomerically pure aryl, hetero aryl and alkyl sulfinimides catalyzed by recyclable tungstophosphoric acid

A simple and efficient procedure was developed for the preparation of a variety of aryl, hetero aryl and alkyl N-sulfinylimines (2b-2u) with excellent yields (85–94%) using tungstophosphoric acid as catalyst. Also, this new synthetic protocol features hig

Triisopropyl borate mediated N-sulfinyl imine formation

Triisopropyl borate effects the condensation of aldehydes with sulfinamides to give N-sulfinyl imines. The reaction is amenable to 1°, 2°, and 3° alkyl aldehydes, as well as aryl, heteroaryl, and α,β-unsaturated aldehydes. In addition to tert-butanesulfin

A General Method for Imine Formation Using B(OCH2CF3)3

Tris(2,2,2-trifluoroethyl)borate [B(OCH2CF3)3] was found to be a mild and general reagent for the formation of a variety of imines by condensation of amides or amines with carbonyl compounds. N-Sulfinyl, N-toluenesulfonyl,

Synthesis of chiral aziridines through decarboxylative generation of sulfur ylides and their reaction with chiral sulfinyl imines

Reaction of sulfur ylides with a series of aryl substituted chiral nonracemic sulfinyl imines afforded the corresponding aziridines in good yields with good stereoselectivity. The sulfur ylides were generated by the thermally induced decarboxylation of carboxymethylsulfonium betaines. A drop in the diastereomeric ratio was observed when going from electron-deficient to electron-releasing aryl substituted imines. S-Methylene aziridinations involving the decarboxylation of carboxymethylsulfonium betaine functionality complements existing technologies with the advantages of the reaction protocol, levels of conversion, and scope.

Conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides using arene borylation

A two-step conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides is described. In this procedure, arenes are converted to aryl boronic esters by iridium-catalyzed borylation, and the aryl boronic esters are converted to enantioenriched amines by subsequent rhodium-catalyzed addition to chiral tert-butanesulfinimes.

KHSO4-mediated condensation reactions of tert-butanesulfinamide with aldehydes. Preparation of tert-butanesulfinyl aldimines

Optically pure tert-butanesulfinyl aldimines 1 were prepared by direct condensation of chiral tert-butanesulfinamide 3 with aldehydes 2 in high yields in the presence of KHSO4. The main advantage of KHSO4 is that it is applicable to the condensation reactions of a variety of aldehydes, including electron deficient and electron rich (hetereo)aromatic aldehydes, as well as aliphatic aldehydes.

Synthesis of Sulfinimines by Direct Condensation of Sulfinamides with Aldehydes Using Cs2CO3 as an Activating and Dehydrating Reagent

Chiral sulfinimines were prepared from chiral sulfinamides and aldehydes in CH2Cl2 in the presence of cesium carbonate as an amine-activating and dehydrating reagent.