82776-14-5

Upstream product

• 6298-96-0 1-(4-methoxyphenyl)ethanamine 
• 108-24-7 acetic anhydride 
• 34910-42-4 1-(1-azidovinyl)-4-methoxybenzene 
• 75-05-8 acetonitrile 
• 1515-95-3 p-ethylanisole 
• 1169755-20-7 tert-butyl (3S,4S,5R,αR)-3-[N-benzyl-N-(α-methyl-4'-methoxybenzyl)amino]-4,5-O-isopropylidene-hept-6-enoate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 6298-96-0 (S)-1-(4-methoxyphenyl)ethylamine 
• 64-19-7 acetic acid 
• 14429-17-5 anti-N-(α-methyl-4-methoxybenzylidene)benzylamine 
• 874-90-8 4-methoxybenzonitrile 
• 75-36-5 acetyl chloride 
• 177750-10-6 N-(1-(4-methoxy)phenylethyl)acetamide 
• 188198-35-8 [(S)-1-(4-Methoxy-phenyl)-ethyl]-dimethyl-borane 

Downstream Products

• 1384190-90-2 N-(1-{4-[2-(4-isopropoxy-2,3-dimethyl-phenoxy)-thiazol-5-yloxy]-phenyl}-ethyl)-acetamide 
• 1384190-99-1 N-(1-{4-[2-(2-bromo-4-cyclopentyloxy-phenoxy)-thiazol-5-yloxy]-phenyl}-ethyl)-acetamide 
• 947522-58-9 C₁₁H₁₅NO₂ 

Relevant academic research and scientific papers

Biocatalytic, Intermolecular C?H Bond Functionalization for the Synthesis of Enantioenriched Amides

Directed evolution of heme proteins has opened access to new-to-nature enzymatic activity that can be harnessed to tackle synthetic challenges. Among these, reactions resulting from active site iron-nitrenoid intermediates present a powerful strategy to forge C?N bonds with high site- and stereoselectivity. Here we report a biocatalytic, intermolecular benzylic C?H amidation reaction operating at mild and scalable conditions. With hydroxamate esters as nitrene precursors, feedstock aromatic compounds can be converted to chiral amides with excellent enantioselectivity (up to >99 % ee) and high yields (up to 87 %). Kinetic and computational analysis of the enzymatic reaction reveals rate-determining nitrenoid formation followed by stepwise hydrogen atom transfer-mediated C?H functionalization.

P-Stereogenic N-Phosphine-Phosphite Ligands for the Rh-Catalyzed Hydrogenation of Olefins

We have identified a successful family of simple P-stereogenic N-phosphine-phosphite ligands for the Rh-catalyzed asymmetric hydrogenation of olefins. These catalysts show excellent enantiocontrol for α-dehydroamino acid derivatives and α-enamides (ee's u

Diaza-Crown Ether-Bridged Chiral Diphosphoramidite Ligands: Synthesis and Applications in Asymmetric Catalysis

A small library of diaza-crown ether-bridged chiral diphosphoramidite ligands was prepared. In the rhodium-catalyzed asymmetric hydrogenation and hydroformylation reactions, these ligands exhibited distinct properties in catalytic activity and/or enantioselectivity. Hydrogenated products with opposite absolute configurations could be obtained in high yields with excellent ee values by utilizing (S,S)-L1 and (S,S)-L3, respectively. Meanwhile, the addition of alkali metal cations caused variations in catalytic outcomes, showing the supramolecular tunability of these Rh/diphosphoramidite catalytic systems.

New chiral ferrocene/indole-based diphosphine ligands for Rh-catalyzed asymmetric hydrogenation of functionalized olefins

Convenient synthesis of a new family of chiral ferrocene/indole-based diphosphine ligands, (Rc,Rp)-IndoFerroPhos (L), from (Sc,Rp)-PPFA and 2-(diphenylphosphino)indole has been described. These new ligands exhibited high efficiency in the Rh-catalyzed asymmetric hydrogenation of functionalized olefins including α-dehydroamino acid esters, α-enamides and dimethyl itaconate, in which up to >99% yield and 98% ee were achieved.

Asymmetric Synthesis of Chiral Primary Amines by Ruthenium-Catalyzed Direct Reductive Amination of Alkyl Aryl Ketones with Ammonium Salts and Molecular H2

A ruthenium/C3-TunePhos catalytic system has been identified for highly efficient direct reductive amination of simple ketones. The strategy makes use of ammonium acetate as the amine source and H2 as the reductant and is a user-friendly and operatively simple access to industrially relevant primary amines. Excellent enantiocontrol (>90% ee for most cases) was achieved with a wide range of alkyl aryl ketones. The practicability of this methodology has been highlighted by scalable synthesis of key intermediates of three drug molecules. Moreover, an improved synthetic route to the optimal diphosphine ligand C3-TunePhos is also presented.

A Single Lipase-Catalysed One-Pot Protocol Combining Aminolysis Resolution and Aza-Michael Addition: An Easy and Efficient Way to Synthesise β-Amino Acid Esters

A novel one-pot protocol combining aza-Michael addition and aminolysis resolution was developed to obtain chiral β-amino acid esters with lipase B from Candida antarctica (CAL-B) as the only catalyst. This method is conducted under mild reaction conditions and is very easy to handle. After a series of detailed optimization studies, ten racemic aromatic or aliphatic amines were subjected to this one-pot procedure, and twelve chiral β-amino acid esters and ten chiral amides were successfully synthesised with excellent ee values in theoretical yields. Scaled-up procedures also worked without apparent reduction in reaction rate or enantioselectivity, which makes this method suitable for large-scale production of chiral β-amino acid esters. A one-pot protocol for simultaneous synthesis of chiral β-amino acid esters and amides was developed by combining single lipase B from Candida antarctica (CAL-B) catalysed aza-Michael addition and aminolysis resolution. This method requires mild reaction conditions and is very easy to handle. Chiral β-amino acid esters and chiral amides were obtained with excellent ee values and in theoretical yields.

Synthesis of phospholane-phosphoramidite ligands and their application in asymmetric catalysis

A set of phospholane-phosphoramidite ligands, which possess four elements of chirality, has been synthesized through a modular diastereoselective process. The ligands were applied in the Rh-catalyzed asymmetric C =C hydrogenation of several functionalized olefins with enantioselectivities of up to 99 % ee and a turnover frequency of up to 12 000 h-1, in the Rh-catalyzed hydroformylation of vinyl arenes with enantioselectivities of up to 79 % ee, and in the Ir-catalyzed asymmetric C =N hydrogenation of different aryl imines with enantioselectivities of up to 79 % ee. New P,P′ hybrid ligands: A set of phospholane-phosphoramidites (quinaphoslane) with four elements of chirality are synthesized through a modular diastereoselective process and applied in the Rh-catalyzed hydrogenation of functionalized olefins with up to 99 % ee and a turnover frequency (TOF) of up to 12 000 h-1, in the Rh-catalyzed hydroformylation of vinyl arenes with regioselectivities of up to 99 % and up to 79 % ee, and in the Ir-catalyzed hydrogenation of imines with up to 79 % ee.

Rh-catalyzed asymmetric hydrogenation using a furanoside monophosphite second-generation ligand library: Scope and limitations

The ligand design of one of the most successful monophosphite ligand classes in Rh-catalyzed hydrogenation was expanded upon by introducing several substituents at the C-3 position of the furanoside backbone. A small but structurally important library of

Rhodium-catalyzed enantioselective hydrogenation of oxime acetates

Rh-catalyzed enantioselective hydrogenation of oxime acetates was first reported, which afforded a new approach for chiral amine synthesis.

Practical enantioselective hydrogenation of α-aryl- and α-carboxyamidoethylenes by rhodium(I)-{1,2-bis[(o-tert-butoxyphenyl) (phenyl)phosphino]ethane}

The rhodium(I)-{1,2-bis[(o-tert-butoxyphenyl)(phenyl)phosphino]ethane} [Rh(I)-(t-Bu-SMS-Phos)] catalyst system displayed prime efficiency in the hydrogenation of large series of aamidostyrenes and a-amidoacrylates. Up to >99.9% enantiomeric excesses coupl