499240-16-3

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 590-86-3 isovaleraldehyde 
• 1323310-68-4 N-(3-methyl-1-(phenylsulfonyl)butyl)-p-toluenesulfonamide 

Downstream Products

• 1132667-84-5 diethyl 2-(3-methyl-1-(4-methylphenylsulfonamido)butyl)malonate 
• 1264626-23-4 N-(1-(1-hydroxynaphthalen-2-yl)-3-methylbutyl)-4-methylbenzenesulfonamide 
• 1344027-05-9 C₁₄H₂₂N₂O₄S 
• 1374450-39-1 (R)-tert-butyl-6-bromo-1-((S)-3-methyl-1-(4-methylphenylsulfonamido)butyl)-3-oxo-1,3-dihydroisobenzofuran-1-carboxylate 
• 1132667-81-2 diethyl 3-isobutyl-1-tosylaziridine-2,2-dicarboxylate 
• 1446528-49-9 C₃₀H₄₄N₂O₅S 
• 1446528-55-7 C₃₀H₄₄N₂O₅S 

Relevant academic research and scientific papers

Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N -Sulfonyl Aldimines

A new copper-catalyzed enantioselective aza-Freidel-Crafts reaction between phenols and N-sulfonyl aldimines that provides chiral secondary benzylamines in good to excellent yields and excellent enantioselectivities (up to 99% ee) is disclosed. In particular, excellent scope with alkylimines was observed for the first time. The synthetic utility of the products was demonstrated in the first enantioselective synthesis of a dual orexin receptor antagonist, a compound that contains an amine-bearing stereocenter adjacent to a bis-ortho-functionalized arene.

Rhodium-Catalyzed Enantioselective Arylation of Aliphatic Imines

Chiral rhodium(I)-catalyzed highly enantioselective arylation of aliphatic N-sulfonyl aldimines with arylboronic acids has been developed. This transformation is achieved by the use of a rhodium/bis(phosphoramidite) catalyst to give enantiomerically enriched α-branched amines (up to 99 % ee). In addition, this system enables efficient synthesis of (+)-NPS R-568 and Cinacalcet which are calcimimetic agents.

A general aminocatalytic method for the synthesis of aldimines

A general and efficient biomimetic method for the synthesis of aldimines from aldehydes and compounds bearing the NH2 group in the presence of pyrrolidine as a catalyst has been developed. These organocatalytic reactions, based on the application of the concept of nucleophilic catalysis, proceed with outstanding yields in the absence of acids and metals under simple conditions and minimum experimental manipulation. The method has been mainly applied to the synthesis of N-sulfinyl and N-sulfonyl imines, but its general validity has been proven with the preparation of representative N-phosphinoyl, N-alkyl, and N-aryl imines. These unprecedented reactions, which presumably occur via iminium activation without requiring acidic conditions, are an interesting and competitive alternative to the classical methods for preparing aldimines.

Highly enantioselective arylation of N -tosylalkylaldimines catalyzed by rhodium-diene complexes

A highly enantioselective rhodium-catalyzed arylation of aliphatic N-tosylaldimines has been developed. The combination of chiral bicyclo[3.3.0]octadiene ligands, an active rhodium hydroxide complex, and neutral reaction conditions is the key to achieving high yield and enantioselectivity. The application of this method is demonstrated by the enantioselective synthesis of chiral 2-aryl pyrrolidines and piperidines in a one-pot procedure. Furthermore, excellent results are also obtained for the imine substrates with the more readily cleavable N-nosyl protecting group.

Direct synthesis of aliphatic vinyl aziridines

The synthesis of vinyl aziridines, by the reactions of a range of diphenylphosphinyl and p-toluenesulfonyl alkyl aldimines with the ylide derived from S-allyl tetrahydrothiophenium bromide, are reported.