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

ABSTRACT: Selenium-containing amino acids are valuable targets but methods for the stereoselective α-selenation of simple amino acid precursors are rare. We herein report the enantioselective electrophilic α-selenation of azlactones (masked α-amino acid derivatives) and isoxazolidin-5-ones (masked β-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.

SUBMITTER: Haider V

PROVIDER: S-EPMC8790592 | biostudies-literature | 2022 Jan

REPOSITORIES: biostudies-literature

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

Haider Victoria V Zebrowski Paul P Michalke Jessica J Monkowius Uwe U Waser Mario M

Organic & biomolecular chemistry 20220126 4

Selenium-containing amino acids are valuable targets but methods for the stereoselective α-selenation of simple amino acid precursors are rare. We herein report the enantioselective electrophilic α-selenation of azlactones (masked α-amino acid derivatives) and isoxazolidin-5-ones (masked β-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 conc ...[more]

PMID: 35015015

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