79138-04-8

Upstream product

• 2517-76-2 3-iodopropanenitrile 
• 103-80-0 phenylacetyl chloride 
• 107-13-1 acrylonitrile 
• 109853-53-4 3-(2-phenylacetyl)-1,3-oxazolidin-2-one 
• 79137-56-7 (S)-3-phenyl-2-(2,4,6-trimethylbenzamido)propanoic acid 
• 79137-67-0 4-Benzyl-2-(2,4,6-trimethyl-phenyl)-4H-oxazol-5-one 
• 7364-51-4 N,O-bis(trimethylsilyl)phenylalanine 
• 79137-85-2 N-Mesitoyl-α-(2-cyanethyl)phenylalanin 

Downstream Products

• 165821-71-6 (S)-5-phenyl-4-hydroxypentanenitrile 
• 165821-76-1 Methanesulfonic acid (S)-1-benzyl-3-cyano-propyl ester 
• 63328-13-2 (R)-2-benzylpyrrolidine 

Relevant academic research and scientific papers

Can decarbonylation of acyl radicals be overcome in radical addition reactions? En route to a solution employing n-acyl oxazolidinones and Sml 2/H2O

The application of acyl radicals in radical addition reactions in the absence of a CO atmosphere is generally limited to aryl or α-unsubstituted alkyl acyl radicals due to competing decarbonylations where the rate constant for this degradation process surpasses 104 s-1. In this work, a potential solution to avoid the problem of decarbonylations is presented employing N-acyl oxazolidinones which are reduced to acyl radical equivalents in the presence of samarium diiodide and water. In the company of an acrylamide, acrylate, or acrylonitrile, the product from a formal acyl radical addition is obtained in yields up to 87%. Examples are given where the decarbonylation rate constants even exceed 108 s-1. It is proposed that the reaction proceeds via a ketyl-like intermediate. Copyright

Enantioselective synthesis of 2-substituted pyrrolidines from 4-hydroxynitriles. Application to the synthesis of the dopamine agonist RS-59022

Two novel routes to optically active 4-hydroxynitriles and the subsequent cyclization to 2-substituted pyrrolidines are described. The methodology is applied to the synthesis of the key intermediate used in the synthesis of the dopamine agonist RS-59022. Unusual selectivity in the CBS reduction of 4-oxonitriles is explained through structural and mechanistic analysis.

α-Aminosaeuren als nucleophile Acylaequivalente, V. Sterisch gelenkte Michael-Addition von Oxazolin-5-on-Anionen an aktivierte Doppelbindungen; Synthese von 1,4-Dicarbonylverbindungen und γ-Oxonitrilen

Oxazolin-5-ones with bulky substituents like mesityl or 1-butylcyclohexyl at C-2 undergo triethylamine catalyzed addition to activated olefins exclusively at C-4.Hydrolysis of the derived 4,4-disubstituted 2-mesityl-2-oxazolin-5-ones 9 leads to N-mesitoyl