870559-17-4

Basic information

• Product Name: (4S,5S)-2-(chloromethyl)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazole
• Synonyms: (4S,5S)-2-(chloromethyl)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazole
• CAS NO: 870559-17-4
• Molecular Weight: 424.951
• Mol File: 870559-17-4.mol

Chemical Properties

• CAS DataBase Reference: (4S,5S)-2-(chloromethyl)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazole(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-2-(chloromethyl)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazole(870559-17-4)
• EPA Substance Registry System: (4S,5S)-2-(chloromethyl)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazole(870559-17-4)

Safety Data

• Hazardous Substances Data: 870559-17-4(Hazardous Substances Data)

Upstream product

• 29841-69-8 (S,S)-1,2-diphenyl-1,2-diaminoethane 
• 870559-13-0 (4S,5S)-2-(chloromethyl)-4,5-dihydro-4,5-diphenyl-1H-imidazole 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1009582-71-1 (1S)-N-{[(4S,5S)-4,5-dihydro-4,5-diphenyl-1-tosyl-1H-imidazol-2-yl]methyl}-1-phenylethanamine 

Relevant articles and documents

Asymmetric Friedel-Crafts reaction of N-heterocycles and nitroalkenes catalyzed by imidazoline-aminophenol-Cu complex

Catalytic asymmetric Friedel-Crafts reaction of pyrrole with nitroalkenes was smoothly catalyzed by newly synthesized nitro-substituted imidazoline-aminophenol (1b)-Cu complex to give the adduct with up to 92% ee.

A library of chiral imidazoline-aminophenol ligands: Discovery of an efficient reaction sphere

A library of imidazolineaminophenol ligands was synthesized on solid supports. After immobilization of chiral chloromethylimidazolines 1 and 2 onto the polystyrylsulfonyl chloride, nucleophilic substitution with (R)-or (S)-phenylethylamine (3 and 4) provided four combinations of polymersupported imidazoline-amine ligands. Further reductive alkylation using salicylaldehydes 7-10 provided a series of imidazoline-aminophenol ligands (L9-L24). Analysis by solid-phase catalysis/circular dichroism high-throughput screening of a copper-catalyzed Henry reaction revealed that ligand L25, comprising a (5,5)-diphenylethylenediamine-derived imidazoline, (S)-phenylethylamine, and dibromophenol, was highly efficient, thus providing the adduct of nitromethane and benzaldehyde in 95 % ee. The combination of stereogenic centers was crucial in promoting the highly stereoselective reactions. The unique reaction sphere of L25 was also examined in a Friedel-Crafts alkylation of indole and nitroalkene to give the adduct in up to 83% ee.

Kinetic resolution of 1,2-diols using nitrogen-tethered bisimidazoline-copper(I) catalyzed benzoylation

Nitrogen-tethered bisimidazoline (Nb-imidazoline) ligand was utilized in the Cu(I)-catalyzed benzoylation of 1,2-diols. With the assistance of i-Pr2NEt, the reaction of rac-1,2-diols with o-methylbenzoyl chloride was smoothly catalyzed by Nb-imidazoline-CuCl in CH2Cl2 to give the corresponding o-methylbenzoylated secondary alcohols in up to 79% ee.

Design and synthesis of a chiral N-tethered bis(imidazoline) ligand

A chiral nitrogen-tethered bis (imidazoline) ligand (Nb-imidazoline) was newly designed and synthesized in a divergent strategy. Thus, a single coupling reaction of primary amine with two molecules of chloromethylated imidazoline provided the Nb-imidazoline. The copper(II) triflate complex of Nb-imidazoline catalyzed a trans-selective cyclopropanation of styrene with ethyl diazoacetate to give the adduct in high chemical yield with good enantiomeric excess up to 83%. Georg Thieme Verlag Stuttgart.