485809-13-0

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 440357-42-6 N,N-dimethyl(triphenylsilyl)acetamide 
• 62285-47-6 2-diazo-N,N-dimethyl-acetamide 
• 485809-19-6 5-phenyl-2-pentenoic acid chloride 
• 124-40-3 dimethyl amine 
• 433231-65-3 C₂₂H₁₆F₁₂NO₃P 

Downstream Products

• 485809-26-5 (2R,3S)-3-phenethyl-oxirane-2-carboxylic acid dimethylamide 

Relevant academic research and scientific papers

Diazo reagents in copper(I)-catalyzed olefination of aldehydes

The olefination of aldehydes to synthesize unsaturated ketones, esters, amides and phosphonates using diazo reagents and triphenylphosphine in the presence of copper(I) iodide as catalyst, is described. Good to excellent E:Z selectivities as well as yields were obtained for a large variety of aliphatic, aromatic and heteroaromatic aldehydes. The reaction showed also an excellent functional group compatibility and aldehydes were selectively reacted in the presence of ketone, nitro, amine, ether, acetal, thioether and halide groups. The use of a cost-effective copper salt as a catalyst is advantageous compared to previously reported expensive transition metal complexes. The method was used in the total synthesis of the scutifoliamide A, a biologically active compound that exhibits antifungal activity.

Catalytic asymmetric epoxidation of α,β-unsaturated amides: Efficient synthesis of β-aryl α-hydroxy amides using a one-pot tandem catalytic asymmetric epoxidation - Pd-catalyzed epoxide opening process

The catalytic asymmetric epoxidation of α,β-unsaturated amides using Sm-BINOL-Ph3As=O complex was succeeded. Using 5-10 mol % of the asymmetric catalyst, a variety of amides were epoxidized efficiently, yielding the corresponding α,β-epoxy amides in up to 99% yield and in more than 99% ee. Moreover, the novel one-pot tandem process, one-pot tandem catalytic asymmetric epoxidation-Pd-catalyzed epoxide opening process, was developed. This method was successfully utilized for the efficient synthesis of β-aryl α-hydroxy amides, including β-aryllactyl-leucine methyl esters. Interestingly, it was found that beneficial modifications on the Pd catalyst were achieved by the constituents of the first epoxidation, producing a more suitable catalyst for the Pd-catalyzed epoxide opening reaction in terms of chemoselectivity. Copyright

Z-selective synthesis of α,β-unsaturated amides with triphenylsilylacetamides

With the purpose of developing a method of preparing Z-α,β-unsaturated amides, the Peterson reaction of the (triphenylsilyl)acetamide Ph3SiCH2COX (1, X = NBn2; 3, X = NMe2) with various aldehydes was examined. The reaction of aromatic aldehydes gave selectivities up to >97:3. It was found that the selectivity was a function of the electronic nature of the aromatic ring and higher Z selectivity was attained with electron-rich aldehydes. With aliphatic aldehydes selectivities up to 92:8 were achieved, and unlike with analogous phosphorus reagents, less sterically hindered aldehydes gave higher Z selectivity. Also, 3, which has a smaller amide group than 1, tended to give rise to higher selectivity. A comparison with the reaction of trimethylsilyl analogues revealed the significance of the phenyl substituents on the silyl group.

Highly Z-selective synthesis of disubstituted α, β-unsaturated cyanides and amides using 10-P-5 wittig type reagents

Phosphoranes (10-P-5) bearing cyanomethyl, acetamide, and N, N-dimethylacetamide groups were examined for Wittig type reactions. All three reacted to give the corresponding olefins. The reaction of the cyanomethyl reagent with aldehydes gave α, β-unsatura