3789-61-5

Usage

Class

Amines

Chirality

Chiral molecule with a stereocenter at the alpha-carbon

Enantiomer

(R)-enantiomer

Usage

Building block in organic synthesis and pharmaceuticals, intermediate in the synthesis of various pharmaceutical compounds, production of pesticides, dyes, and other organic compounds

Therapeutic Applications

Potential anti-inflammatory and anticancer agent

Upstream product

• 66558-08-5 4-Methyl-benzenesulfinic acid ((S)-naphthalen-1-yl-phenyl-methyl)-amide 
• 16635-23-7 phenyltriisopropoxytitanium(IV) 
• 100-47-0 benzonitrile 
• 866993-20-6 (S)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 
• 138258-94-3 (1R,1'R)-2'-Hydroxy-1'-(phenylethyl)-1-(1-naphthyl)-phenylmethylamine 
• 66558-07-4 (R)-4-methyl-N-(naphthalen-1-yl(phenyl)methyl)benzenesulfonamide 

Downstream Products

• 66558-07-4 (R)-4-methyl-N-(naphthalen-1-yl(phenyl)methyl)benzenesulfonamide 

Relevant academic research and scientific papers

Enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids

The asymmetric arylation of N-tosylarylimines with arylboronic acids was realized by using rhodium/(S)-ShiP as catalyst. The reaction proceeded in aqueous toluene to give diarylmethylamines in good yields with up to 96% ee.

Asymmetric synthesis of diarylmethyl amines by rhodium-catalyzed asymmetric addition of aryl titanium reagents to imines

A rational tuning of the arene sulfonamide moiety (by introducing isopropyl groups onto the phenyl ring) brought about high enantioselectivity in the asymmetric synthesis of diarylmethyl amines by the title reaction (see scheme). Ar1 = 4-CF3C6H4, 4-ClC 6H4, 4-FC6H4, 3-MeOC 6H4, 4-MeOC6H4, 2-MeC 6H4, 1-naphthyl, Ph; Ar2 = Ph, 4-FC 6H4, 3-MeOC6H4, 4-MeOC 6H4.

Lead tetraacetate cleavage of chiral phenylglycinol derived secondary amines without racemization

Diastereomerically enriched N-(1,1-disubstituted methyl)(2'-hydroxy-1'-phenylethyl)amines were oxidatively converted to enantiomerically enriched primary disubstituted methylamines in excellent yields without racemization, using an improved lead tetraacetate (LTA) procedure.

Asymmetric Induction in the Reduction of Optically Active N-Alkylidenesulphinamides by Metal Hydrides. A New, Efficient Enantioselective Route to Chiral Amines

A series of racemic and optically active N-alkylidenesulphinamides has been prepared and their reduction by metal hydrides studied.The extent of asymmetric synthesis mainly depends on the nature of the reducing species; the best results (up to 92percent of stereoselectivity) are obtained with alkoxy-lithium aluminium hydrides.A new, highly enantioselective synthesis of amines is described.