317366-88-4

Upstream product

• 64-04-0 phenethylamine 
• 104-55-2 3-phenyl-propenal 
• 100-52-7 benzaldehyde 
• 98-80-6 phenylboronic acid 
• 63-91-2 L-phenylalanine 

Downstream Products

• 907554-94-3 C₁₈H₁₈N₂ 
• 1421426-92-7 N-phenethylcinnamimidoyl cyanide 
• 1392216-47-5 7,8-dihydro-7,7-dimethyl-1-phenethyl-4-phenylquinolin-5(1H,4H,6H)-one 

Relevant academic research and scientific papers

Development of Chiral Spiro Phosphoramidites for Rhodium-Catalyzed Enantioselective Reactions

A series of 1,1′-spirobiindane-7,7′-diol (SPINOL) analogues bearing a 2,2′-dimethyl-, cyclopentyl-, or cyclohexyl-fused ring were synthesized, and their distinct structural features were elucidated by X-ray crystallography. On the basis of these scaffolds, chiral monophosphoramidite ligands 6 a–m were synthesized, which demonstrated excellent enantioselectivity in RhI-catalyzed asymmetric hydrogenation of a dehydro amino acid methyl ester. Ligands 6 a–m were also successfully applied in the RhI-catalyzed enantioselective [4+2] cycloaddition of α,β-unsaturated imines with isocyanates, which afforded the corresponding pyrimidinones in good yields (60–92 %) with high enantioselectivities (75–92 % ee).

Silylative Reductive Amination of α,β-Unsaturated Aldehydes: A Convenient Synthetic Route to β-Silylated Secondary Amines

Described here is a reductive amination/hydrosilylation cascade of α,β-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards β-silylated secondary amines that have not been accessible by other previous catalysis. Comparative 1H NMR studies on the silylative reduction of enimines revealed that steric bulkiness of primary amine reactants strongly affects both catalytic efficiency and regioselectivity. This strategy was applicable to a broad range of substrates and amenable to one-pot gram-scale synthesis. Moreover, a diastereoselective introduction of the β-silyl group was also found to be feasible (d.r. up to 71:29).

Aromatic aldehyde-catalyzed gas-phase decarboxylation of amino acid anion via imine intermediate: An experimental and theoretical study

It is generally appreciated that carbonyl compound can promote the decarboxylation of the amino acid. In this paper, we have performed the experimental and theoretical investigation into the gas-phase decarboxylation of the amino acid anion catalyzed by the aromatic aldehyde via the imine intermediate on the basis of the tandem mass spectrometry (MS/MS) technique and density functional theory (DFT) calculation. The results show that the aromatic aldehyde can achieve a remarkable catalytic effect. Moreover, the catalytic mechanism varies according to the type of amino acid: (i) The decarboxylation of α-amino acid anion is determined by the direct dissociation of the C-C bond adjacent to the carboxylate, for the resulting carbanion can be well stabilized by the conjugation between α-carbon, C=N bond and benzene ring. (ii) The decarboxylation of non-α-amino acid anion proceeds via a SN2-like transition state, in which the dissociation of the C-C bond adjacent to the carboxylate and attacking of the resulting carbanion to the C=N bond or benzene ring take place at the same time. Specifically, for β-alanine, the resulting carbanion preferentially attacks the benzene ring leading to the benzene anion, because attacking the C=N bond in the decarboxylation can produce the unstable three or four-membered ring anion. For the other non-α-amino acid anion, the C=N bond preferentially participates in the decarboxylation, which leads to the pediocratic nitrogen anion.

Synthesis of iminonitriles by oxone/tbab-mediated one-pot oxidative three-component strecker reaction

Oxidative three-component reaction of aldehydes, amines, and TMSCN in a biphasic solvent system (toluene/H2O) containing Oxone, tetra-n-butylammonium bromide (TBAB) and sodium bicarbonate afforded α-iminonitriles in good to excellent yields. This oxidative Strecker reaction was applicable to a wide range of aldehydes and amines, aromatic or aliphatic, of different electronic and steric properties. Substituted 1-aza-2-cyano-1,3-dienes were also accessible using α,β-unsaturated aldehydes as inputs.

Efficient synthesis of N-Substituted 4-arylquinoline derivatives using ZnCl2 or ZrO2

N-Substituted 7,8-dihydro-7,7-dimethyl-4-arylquinolin-5(1H,4H,6H)-ones 4a-l have been reported by one-pot reaction of cinnamaldehyde derivatives, dimedone and various amines in the presence of ZnCl2 or ZrO2 in fairly high yields.