Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives

Selenium-containing amino acids are valuable targets but methods for the stereoselective alpha-selenation of simple amino acid precursors are rare. We herein report the enantioselective electrophilic alpha-selenation of azlactones (masked alpha-amino acid derivatives) and isoxazolidin-5-ones (masked beta-amino acids) using Cinchona alkaloids as easily accessible organocatalysts. A variety of differently substituted derivatives was accessed with reasonable levels of enantioselectivities and further studies concerning the stability and suitability of these compounds for further manipulations have been carried out as well.

Automated summary

This study presents an enantioselective electrophilic alpha-selenation method using Cinchona alkaloids as organocatalysts, leading to the synthesis of a variety of differently substituted derivatives with reasonable levels of enantioselectivities. Further investigations on the stability and suitability of these compounds for further manipulations have also been carried out.