1393880-66-4

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 106-38-7 para-bromotoluene 
• 1393880-52-8 (E)-methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)-3-(p-tolyl) acrylate 
• 7560-43-2 methyl 3-(4-methylphenyl)acrylate 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1393880-67-5 (S)-methyl 3-((phenylcarbamoyl)oxy)-3-(p-tolyl)propanoate 
• 135505-13-4 3-hydroxy-3-(4-methoxyphenyl)-propionic acid methyl ester 

Relevant academic research and scientific papers

Configuration Sampling With Five-Membered Atropisomeric P,N-Ligands

Here we report a strategy for the systematic variation of atropisomeric C1-symmetric P,N ligands to incrementally change the position of the groups within the chiral pocket without modifying their steric parameters. More specifically, the effec

Chiral Bicyclic NHC/Cu Complexes for Catalytic Asymmetric Borylation of α,β-Unsaturated Esters

The potential of using chiral bicyclic NHC ligands that exhibit modularity was investigated in the Cu-catalyzed asymmetric borylation reaction of α,β-unsaturated esters. After screening for ligands and optimization of the reaction conditions, the corresponding products were afforded with good enantioselectivities (up to 85% ee).

Well-Defined Chiral Copper NHC Complex in the Asymmetric Conjugated β-Borylation and One-Pot Metathesis-Asymmetric β-Borylation Reactions

Highly stereoselective conjugate β-borylation, using a new chiral NHC-based copper catalyst, has been achieved. The chiral NHC copper complex was prepared in gram scale and showed high enantioselectivity and activity (up to 10 000 turnovers at 100 ppm of catalyst loading). This method was employed in the synthesis of a chiral β-borylated ester from simple unconjugated alkenes though an unprecedented one-pot cross metathesis-asymmetric borylation sequence.

Facile synthesis of chiral benzimidazolium salts and the application in asymmetric catalytic borylation

A synthetic method towards chiral benzimidazolium salts is developed. The stereocenter is introduced by direct aromatic substitution of 2-fluoronitrobenzene with optically pure amines. After nitro group reduction, selective arylation of the primary amine is achieved via copper catalyzed Chan-Lam coupling reaction. Finally, cyclization of the diamine with HC(OMe)3 afforded the desired chiral benzimidazolium salts. In situ generated benzimidazole carbenes show potential application for asymmetric catalytic borylation of α,β-unsaturated esters, providing up to 85% ee value with a catalyst loading of only 0.5 mol%.

Stereoselective preparation of β-aryl-β-boronyl enoates and their copper-catalyzed enantioselective conjugate reduction

A new methodology has been developed for the stereoselective preparation of β-aryl-β-boronyl α,β-unsaturated esters via Heck coupling, and their subsequent copper(I)-catalyzed enantioselective conjugate reduction. Various chiral secondary boronate derivatives can be accessed in excellent yields and good to high levels of enantioselectivity through the efficient copper-catalyzed process using polymethylhydrosiloxane (PMHS) as the hydride source.