79357-49-6

Upstream product

• 79357-45-2 (E)-N-Acetyl-α,β-didehydronorleucin-methylester 
• 79357-44-1 (Z)-N-Acetyl-α,β-didehydronorleucin-methylester 
• 81629-66-5 (Z)-2-Acetylamino-hex-2-enoic acid methyl ester 
• 56247-43-9 N-acetylnorleucine methyl ester 
• 199539-80-5 (2Z,4E)-methyl 2-acetamidohexa-2,4-dienoate 
• 89524-99-2 methyl 2-acetylamino-2-(dimethoxyphosphinyl)acetate 
• 73198-56-8 N-acetyl-α-methoxyglycine methyl ester 
• 6395-83-1 α-keto methyl hexanoate 
• 79357-41-8 Methyl (E)-2-(chloroacetamido)hex-2-enoate 
• 79357-43-0 Methyl (E)-2-(iodoacetamido)hex-2-enoate 

Relevant academic research and scientific papers

Catalytic Asymmetric Hydrogenation of Methyl (E)- and (Z)-2-Acetamido-3-alkylacrylates

Rhodium-chiral phosphine complex catalyzed homogeneous hydrogenations of methyl (Z)- and (E)-2-acetamido-4-methoxybut-2-enoates ((Z,E)-10), methyl (Z)- and (E)-2-acetamidohex-2-enoates ((Z,E)-16A) and methyl (Z)- and (E)-2-acetamido-4-methylpent-2-enoates ((Z,E)-16B) are reported.With phosphines in which two achiral phosphorus atoms are connected by a chiral four-carbon unit, higher product enantiomeric excesses (ee's) are obtained from E than from Z substrates.With phosphines in which a two-carbon chiral unit separates two achiral phosphorus atoms, Z substrates are preferred.With dipamp (28), both Z and E substrates (particularly (Z,E)-16A) are reduced with high enantioselectivity.The additional oxygen atom in substrates (Z,E)-10 has little effect on product ee with most phosphines.

Highly enantioselective synthesis of non-natural aliphatic α-amino acids via asymmetric hydrogenation

By employing a rhodium-Duanphos complex as the catalyst, β-alkyl (Z)-N-acetyldehydroamino esters were smoothly hydrogenated in a highly efficient and enantioselective way. Excellent enantioselectivities together with excellent yields were achieved for a series of substrates. An efficient approach for the synthesis of the intermediate of the orally administered anti-diabetic drugs Alogliptin and Linagliptin in the DPP-4 inhibitor class was also developed.

Highly enantioselective hydrogenation of α-dehydroamino esters and itaconates with triphosphorous bidentate ligands and the unprecedented solvent effect thereof

(Chemical Equation Presented) An X-ray diffraction experiment revealed an interesting triphosphorous bidentate coordination in a Pd(II) complex of a phosphine-phosphoramidite ligand 1, which showed excellent enantioselectivity (up to 99.4% ee) in Rh-catalyzed hydrogenation of α-dehydroamino esters in acetone. A dramatic solvent effect was found in the hydrogenation of itaconates, which induces opposite chiralities of the product with the same catalytic system by the use of different solvents (e.g., 99.6% ee (R) in TFE vs 71.2% ee (S) in methyl ethyl ketone).

One-pot tandem enantioselective hydrogenation-hydroformylation synthesis of cyclic α-amino acids

Five- and six-membered cyclic amino acids can be prepared in good yield with high ee (> 95%) via tandem rhodium-DuPHOS catalysed asymmetric hydrogenation followed by a rhodium-catalysed hydroformylation-cyclisation sequence in a single pot. The synthesis can be achieved using Rh-DuPHOS as the sole catalyst.

Pronase catalysed peptide syntheses

A mixture of proteases from Streptomyces griseus (pronase), displaying a very broad substrate tolerance in the hydrolysis of peptides, has been studied for the first time systematically regarding their substrate specificity in peptide synthesis. It is demonstrated that pronase can be employed successfully for the formation of dipeptides with yields up to 95%. Pronase has also been employed successfully as catalyst for the enzyme assisted synthesis of a hexapeptide.

Preparation and use of C2-symmetric bis(phospholanes): Production of α-amino acid derivatives via highly enantioselective hydrogenation reactions

A new class of chiral C2-symmetric bis(phospholane) ligands has been prepared and used in rhodium-catalyzed asymmetric hydrogenation reactions. We describe a practical, one-pot procedure which utilizes enantiomerically pure 1,4-diol cyclic sulf