292066-56-9

Upstream product

• 17887-55-7 2-trimethylsilylbenzaldehyde 
• 105123-35-1 2,4,6-tris([1,1'-biphenyl]-4-yl)boroxine 
• 738626-27-2 (R)-N-[(1,1'-biphenyl-4-yl)(phenyl)methyl]-4-methylbenzenesulfonamide 
• 220441-81-6 C-(4-bromo-phenyl)-C-phenyl-methylamine 
• 98-80-6 phenylboronic acid 
• 172794-72-8 benzyl N-benzylidenecarbamate 
• 108-95-2 phenol 
• 5122-94-1 4-biphenylboronic acid 
• 738626-26-1 (+)-N-{4-biphenyl-[2-(trimethylsilyl)phenyl]methyl}-4-methylbenzenesulfonamide 
• 738626-16-9 N-[2-(trimethylsilyl)benzylidene]-4-methylbenzenesulfonamide 

Downstream Products

• 292066-60-5 (R)-(+)-α-(4-biphenylyl)-N-(2,2-dimethoxyethyl)benzylamine 
• 91487-86-4 (R)-(-)-1-[α-(4-biphenylyl)benzyl]-1H-imidazole 
• 292066-62-7 (R)-(-)-N-[α-(4-biphenylyl)benzyl]-N-(2,2-dimethoxyethyl)formamide 

Relevant academic research and scientific papers

Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-friedel-crafts reaction of phenols

Chiral BINOL-derived pyrophosphoric acid catalysts were developed and used for the regio- and enantioselective aza-Friedel-Crafts reaction of phenols with aldimines. ortho/para-Directing phenols could react at the para-position selectively with moderate to good enantioselectivities. Moreover, the gram-scale transformation of a product into the key intermediate for the antifungal agent (R)-bifonazole was demonstrated.

Design and Synthesis of Chiral Diene Ligands for RhI-Catalyzed Enantioselective Arylation of N-DPP-protected Aldimines: Synthesis of the Antifungal Agent Bifonazole

Herein we describe the design and synthesis of a novel family of bifunctional, chiral bicyclo[2.2.1]heptadiene ligands bearing aryl and secondary amido groups, and demonstrate their usefulness in the RhI-catalyzed enantioselective addition reaction of arylboronic acids to N-diphenylphosphinyl (N-DPP)-protected aldimines. Unlike the analogous RhI-catalysts comprising diene ligands substituted with aryl and carboxylic ester groups, or only with aryl groups, the addition reaction proceeded with high stereoselectivity. The protocol tolerated a range of N-DPP-aldimines and arylboronic acids, producing the desired optically active N-DPP-protected amines with yields between 31–99 % and with ee values up to 91–99 %. The synthetic utility of the method was demonstrated by the conversion of N-DPP-protected amine 3 ae into the antifungal agent, bifonazole (13).

Practical syntheses of enantiomerically pure N-acetylbenzhydrylamines

Two practical routes for the synthesis of benzhydrylamine derivatives in enantiomerically pure form have been developed. N-Acetylbenzhydrylamines can be synthesised in few steps and good yields starting from 1-aryl-1-propargylamines. The key steps are rep

N-Boc-L-valine-connected amidomonophosphane rhodium(I) catalyst for asymmetric arylation of N-tosylarylimines with arylboroxines

A catalytic asymmetric arylation of sterically tuned imines with arylboroxines was developed by using N-Boc-L-valine-connected amidomonophosphane rhodium(I) catalyst in n-PrOH. The TMS group used for the steric tuning of imines is convertible to other fun