38526-14-6

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 119072-55-8 tert-butylisonitrile 
• 1779-48-2 phenylphosphinic acid 
• 22336-21-6 (4-chlorophenyl)phosphinic acid 
• 100-52-7 benzaldehyde 
• 1914-59-6 (E)-2-oxo-4-phenyl-3-butenoic acid 
• 1190946-81-6 (E)-N-(tert-butyl)-2-oxo-4-phenylbut-3-enamide 

Downstream Products

• 31334-65-3 N-(tert-butyl)-2-oxo-4-phenylbutanamide 
• 4263-93-8 2-hydroxy-4-phenylbutanoic acid 

Relevant academic research and scientific papers

Iridium/f-Amphox-Catalyzed Asymmetric Hydrogenation of Styrylglyoxylamides

We report an iridium-catalyzed asymmetric hydrogenation reaction for the preparation of chiral homophenylalanine derivatives. Catalyzed by an iridium/f-amphox complex, the asymmetric hydrogenation of styrylglyoxylamides was conducted smoothly with turnover numbers of up to 10,000 and up to 98% ee. This method was successfully applied in a synthesis of a fragment of benazepril, a drug used for the treatment of high blood pressure.

A one-pot o-phosphinative passerini/pudovik reaction: Efficient synthesis of highly functionalized α-(phosphinyloxy)amide derivatives

A one-pot O-phosphinative Passerini/Pudovik reaction has been developed, based on reacting aldehydes, isocyanides, and phosphinic acids followed by the addition of second aldehydes to form the corresponding α-(phosphinyloxy) amide derivatives. This is the first reported instance of a Passerini-type, isocyanide-based multicomponent reaction using a phosphinic acid instead of a carboxylic acid. The nucleophilicity of the phosphinate group allows a subsequent catalytic Pudovik-type reaction, affording the highly functionalized α-(phosphinyloxy)amide derivative in high yield. A wide range of aldehydes and isocyanides are applicable to this reaction.

Borinic acid catalyzed α-addition to isocyanide with aldehyde and water

A first example of diphenylborinic acid catalyzed α-addition to isocyanide with aldehyde and water is described. The reaction proceeded smoothly in the presence of water and 5 mol % of borinic acid to give the corresponding α-hydroxyamides in good to high

Synthesis and biological evaluation of α-ketoamides as inhibitors of the Dengue virus protease with antiviral activity in cell-culture

The development of small molecule inhibitors of the viral protease is of considerable interest for the treatment of emergent flaviviral diseases such as Dengue or West Nile fever. Until today little progress has been made in finding drug-like compounds th

Catalytic, enantioselective α-additions of isocyanides: Lewis base catalyzed Passerini-type reactions

The generality of catalytic, enantioselective α-additions of isocyanides to aldehydes has been demonstrated (Passerini-type reactions). The catalytic system of silicon tetrachloride and a chiral bisphosphoramide (R,R)-1b provided high yields and good to excellent enantioselectivities for the addition of tert-butyl isocyanide to a wide range of aldehydes (aromatic, heteroaromatic, olefinic, acetylenic, aliphatic). Aqueous workup afforded the α-hydroxy tert-butyl amides whereas a low-temperature methanol quench followed by basic workup afforded the α-hydroxy methyl esters. The reaction is also successful for other isocyanides, albeit with reduced enantioselectivity. Reaction conditions, particularly the rate of addition of the isocyanide was found to be crucial for good yields and high selectivities.

The first catalytic, asymmetric α-additions of isocyanides. Lewis-base-catalyzed, enantioselective Passerini-type reactions

The first, catalytic, enantioselective α-additions of isocyanides to aldehydes have been demonstrated (Passerini-type reactions). The catalytic system of silicon tetrachloride and a chiral bisphosphoramide 5a provided high yields and good to excellent enantioselectivities for the addition of tert-butyl isocyanide to a wide range of aldehydes (aromatic, olefinic, acetylenic, aliphatic). Aqueous workup afforded the α-hydroxy tert-butyl amides, whereas methanolic quench followed by basic workup afforded the ∞-hydroxy methyl esters. Copyright