117266-34-9

Upstream product

• 62-53-3 aniline 
• 1896-62-4 (E)-benzalacetone 

Downstream Products

• 95121-84-9 (S)-(1-methyl-3-phenylallyl)phenylamine 
• 471930-02-6 (R)-(+)-N-(1-methyl-3-phenyl-2-propenyl)aniline 
• 1217341-43-9 (E)-N-(4-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butan-2-ylidene)aniline 
• 74378-59-9 rac-(1RS,3RS)-1-phenyl-3-(phenylamino)butan-1-ol 
• 1619986-36-5 C₁₆H₁₇NO 

Relevant academic research and scientific papers

Highly enantio-and diastereoselective synthesis of Iγ-amino alcohols from α,β-unsaturated imines through a one-pot β-boration/ reduction/oxidation sequence

A simple one-pot three-step synthetic route towards chiral Iγ-amino alcohols has been established. Considering the overall stereocontrol of the synthetic protocol, the first and key step is the enantioselective β-boration of α,β-unsaturated imines. By screening a small library of potential chiral auxiliaries, several chiral phosphorus ligands have been identified which induce exceptional enantioselectivities (up to 99% ee). For the stoichiometric reduction of the imino group, it has been found that high levels of 1,3-diastereocontrol can be achieved using achiral reducing agents. A new methodology for the synthesis of both diastereoisomers, syn and anti, has been established. The last step of the reaction sequence, oxidative substitution of the boryl unit with a hydroxy group, proceeds with complete retention of the configuration at the Cβ-atom. Most importantly, the three simple steps can be carried out in one pot without significant change in the overall stereoselectivity.

Cu(ii)-Catalyzed asymmetric boron conjugate addition to α,β-unsaturated imines in water

Enantioselective conjugate addition of bis(pinacolato)diboron to α,β-unsaturated imines proceeds smoothly in water in the presence of a chiral copper(ii) complex consisting of Cu(OAc)2 and chiral 2,2′-bipyridine. The corresponding β-boryl imines, which were oxidized to β-hydroxy imines, further leading to γ-amino alcohols, were obtained in high yields and high enantioselectivities.

Insertion of Nitriles into Zirconocene 1-aza-1,3-diene Complexes: Chemoselective Synthesis of N-H and N-Substituted Pyrroles

The direct insertion of nitriles into zirconocene-1-aza-1,3-diene complexes provides an efficient, chemoselective, and controllable synthesis of N-H and N-substituted pyrroles upon acidic aqueous work-up. The outcome of the reaction (that is, the formatio

Catalytic 1,3-difunctionalisation of organic backbones through a highly stereoselective, one-pot, boron conjugate-addition/reduction/oxidation process

A simple one-pot, three-step synthetic route to chiral 1,3-amino alcohols and 1,3-diols has been established. Considering the overall stereocontrol of the synthetic protocol, the first and key step is an enantioselective β-boration of α,β-unsaturated imin

Organocatalytic versus iron-assisted β-boration of electron-deficient olefins

Combo effects: The first example of an iron-mediated β-boration of activated olefins is reported. The origin and the benefits of the catalytic activity associated with the presence of iron have been questioned and carefully studied. The iron system has be

Catalytic β-boration/oxidation of 1-azadienes

A highly efficient Cu-catalyzed C-B bond formation has been developed to transform 1-azadienes into β-imino boronate esters when reacted with bis(pinacolato)diboron and a base. A series of functionalized imines and oximes were found to react under very mi

A highly enantioselective Lewis basic organocatalyst for reduction of N-aryl imines with unprecedented substrate spectrum

L-Pipecolinic acid derived formamides have been developed as highly efficient and enantioselective Lewis basic organocatalysts for the reduction of N-aryl imines with trichlorosilane. Catalyst 4b afforded high isolated yields (up to 98%) and enantioselect