260997-46-4

Upstream product

• 934-56-5 trimethyl(phenyl)stannane 
• 260997-38-4 N-(4-chloro-benz-(E)-ylidene)-4-nitro-benzenesulfonamide 
• 3262-89-3 triphenylboroxine 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 260997-38-4 C₁₃H₉ClN₂O₄S 
• 98-80-6 phenylboronic acid 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 163837-32-9 (S)-4-chloro-α-phenyl-benzenemethanamine 

Relevant academic research and scientific papers

Enantioselective and rapid Rh-catalyzed arylation of N -tosyl- and N -nosylaldimines in methanol

Enantiomerically enriched tosyl-protected diarylmethylamines were rapidly prepared by the asymmetric addition of arylboronic acids to N-tosylaldimines under mild conditions in the presence of a catalyst prepared in situ from Rh(I) and a chiral diene ligand. This methodology offers access to diarylmethylamines in good yields with excellent chiral purity at room temperature using MeOH as a solvent and NEt3 as a base. Its synthetic utility was demonstrated by the preparation of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (14), an antagonist of the N-methyl-d-aspartate (NMDA) receptor.

C1-symmetric bicyclo[2.2.2]octa-2,5-diene (bod*) ligands in rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to enones and 1,2-addition to N-[(4-nitrophenyl)sulfonyl]imines

A set of ten C1-symmetric chiral bicyclo[2.2.2]octa-2,5-dienes (bod*) 2 (Fig. 1) were tested as ligands in Rh-catalyzed arylation reactions. The 1,4-addition of arylboronic acids to cyclohex-2-en-1-one, cyclopent-2-en-1-one, and tert-butyl cinn

Highly enantioselective synthesis of (diarylmethyl)amines by rhodium-catalyzed arylation of N-nosylimines using a chiral bicyclo[3.3.0]diene ligand

A highly efficient asymmetric arylation of N-nosylimines with arylboronic acids catalyzed by a rhodium-diene complex is described. A wide range of enantiopure (98-99% ee) N-(diarylmethyl)nosylamides, as well as (3S)-2-(4-nosyl)-3-phenylisoindolin-1-one, were obtained in high yields (83-99%) under very mild conditions. Georg Thieme Verlag Stuttgart New York.

Electronic and steric tuning of chiral diene ligands for rhodium-catalyzed asymmetric arylation of imines

Rhodium-catalyzed asymmetric arylation of imines using electronically and sterically-modified chiral diene ligands gave the corresponding diarylmethylamines in high yield and with high enantioselectivity using just 0.3 mol% of catalyst.

Expanding the C2-symmetric bicyclo[2.2.1]hepta-2,5-diene ligand family: Concise synthesis and catalytic activity in rhodium-catalyzed asymmetric addition

New C2-symmetric bicyclo[2.2.1]hepta-2,5-dienes bearing methyl and phenyl substituents at the 2 and 5 positions were prepared enantiomerically pure through a two-step sequence starting from the readily available bicyclo[2.2.1]hepta-2,5-dione. Due to the instability or volatility of these dienes, their isolation was achieved through the formation of the corresponding stable [RhCl(diene)]2 complexes. These chiral rhodium complexes displayed high activity and enantioselectivity (up to 99% ee) in the rhodium-catalyzed 1,4-addition and 1,2-addition of phenylboronic acid to cyclic enones and N-sulfonylimines, respectively.

C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines

(Chemical Equation Presented) Asymmetric synthesis of diarylmethylamines with high enantioselectivity (95-99percent ee) was realized by use of a new C 2-symmetric diene ligand, (1R,5R)-2,6-diphenylbicyclo[3.3.1]nona-2,6- diene (Ph-bnd*), for th

C2-Symmetric bicyclo[3.3.1]nona-2,6-diene and bicyclo[3.3.2]deca-2,6-diene: New chiral diene ligands based on the 1,5-cyclooctadiene framework

As a new type of C2-symmetric chiral diene ligands, which coordinate to a metal by their 1,5-cyclooctadiene framework, we prepared 2,6-disubstituted bicyclo[3.3.1]nona-2,6-diene (bnd*) and bicyclo[3.3.2]deca-2,6-diene (bdd*), and examined their catalytic activity and enantioselectivity for rhodium-catalyzed asymmetric 1,4-addition to α,β-unsaturated ketones and 1,2-addition to N-sulfonylimines. High enantioselectivity of the Ph-bnd* ligand was observed in the addition of phenylboroxine to N-tosylimine and N-4-nitrobenzenesulfonylimine of 4-chlorobenzaldehyde to give phenyl(4-chlorophenyl)methylamines in high enantiomeric excess (98-99% ee).