81777-37-9

Upstream product

• 81777-35-7 4-Methyl-benzenesulfinic acid ((R)-2-methyl-1-phenyl-propyl)-amide 
• 51608-60-7 N-(benzylidene)-p-methylbenzenesulfonamide 
• 625-81-0 diisopropyl zinc 
• 866993-20-6 (S)-4-methyl-N-(1-phenylethylidene)benzenesulfinamide 
• 100-47-0 benzonitrile 
• 1517-82-4 (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate 
• 51608-60-7 phenyl N-tosyl imine 
• 353264-99-0 N-isobutylidene-4-methylbenzenesulfonamide 
• 98-80-6 phenylboronic acid 
• 70-55-3 toluene-4-sulfonamide 

Relevant academic research and scientific papers

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.

Chiral N-Heterocyclic Carbene Ligands Bearing a Pyridine Moiety for the Copper-Catalyzed Alkylation of N-Sulfonylimines with Dialkylzinc Reagents

Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee). The addition of HMPA to the reaction mixture as a co-solvent is critical in terms of chemical yield and enantioselectivity. A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction. Amino acid-derived chiral imidazolium salts, each bearing a pyridine ring, were developed as N-heterocyclic carbene ligands. The copper-catalyzed asymmetric alkylation of various N-sulfonylimines with dialkylzinc reagents in the presence of these chiral imidazolium salts afforded the corresponding alkylated products with high enantioselectivity (up to 99 % ee; see scheme). A wide range of N-sulfonylimines and dialkylzinc reagents were found to be applicable to this reaction.

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.

Asymmetric Alkylation of N-Toluenesulfonylimines with Dialkylzinc Reagents Catalyzed by Copper-Chiral Amidophosphine

The synthetic procedure of a chiral amidophosphine ligand 5 bearing two bulky substituents, 2,4,6-trimethylphenylmethyl or 2,4,6-triisopropylphenylmethyl groups, on the pyrrolidine ring was improved by employing the borane-THF reduction of the lactam-alco

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.