A concise synthesis of enantiomerically pure aroyl-l-alanines and dihydroaroyl-l-alanines

✍ Scribed by Gardiánová, Mária; Slížik, Ľuboš; Koreňová, Anna; Považanec, František; Berkeš, Dušan

• Book ID: 119932368
• Publisher: Versita
• Year: 2013
• Tongue: English
• Weight: 258 KB
• Volume: 67
• Category: Article
• ISSN: 0366-6352
• DOI: 10.2478/s11696-012-0246-z

✦ Synopsis

Dedicated to Professor Štefan Toma on the occasion of his 75th birthday

Straightforward preparation of enantiomerically highly enriched N-substituted aroylalanines has been developed. This process involves the combination of crystallization-induced asymmetric transformation and a conjugate addition of N-nucleophiles to the corresponding aroylacrylic acids. Further transformations to 3,4-dichlorobenzoylalanine and aroyl-l-alanines via periodate oxidation and stereoselective reduction to N-substituted syn-4-aryl-4-hydroxy-2-aminobutanoic acids are also described.