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. 2022 Jan 26;20(4):824-830.
doi: 10.1039/d1ob02235k.

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

Victoria Haider  1 , Paul Zebrowski  1 , Jessica Michalke  2 , Uwe Monkowius  3 , Mario Waser  1
Affiliations

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

Victoria Haider et al. Org Biomol Chem. .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Targeted organocatalytic electrophilic α-selenation of masked α- and β-AA derivatives 1 and 2.
Fig. 1
Fig. 1. Chiral organocatalysts tested herein.
Scheme 2
Scheme 2. Attempted ring opening of 3a and direct α-selenation of the dipeptide-based azlactone 7.
Scheme 3
Scheme 3. Application scope for the enantioselective α-selenation of azlactones 1.
Scheme 4
Scheme 4. Further manipulations of compound 4a.
Scheme 5
Scheme 5. Application scope for the enantioselective α-selenation of isoxazolidinones 2.
See this image and copyright information in PMC

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