Issue 17, 2022

Synthesis of chiral β-substituted γ-amino-butyric acid derivatives via enantioconvergent ring opening of racemic 2-(hetero)aryl aziridines with ketene silyl acetals

Abstract

Chiral β-substituted γ-amino-butyric acids (GABAs) belong to a class of molecular architectures possessing a high pharmaceutical value. We report herein a straightforward efficient strategy to access such compounds by the Lewis acid-catalyzed asymmetric aminoalkylation reaction of ketene silyl acetals via enantioconvergent ring opening of racemic 2-(hetero)aryl-N-sulfonyl aziridines. This reaction features scalability, simple and commercially available catalysts, high enantioselectivities and mild reaction conditions with demonstrated utility in a two-step product transformation into the anti-inflammatory drug (R)-rolipram and its optical antipode.

Graphical abstract: Synthesis of chiral β-substituted γ-amino-butyric acid derivatives via enantioconvergent ring opening of racemic 2-(hetero)aryl aziridines with ketene silyl acetals

Supplementary files

Article information

Article type
Research Article
Submitted
19 Mar 2022
Accepted
16 Jul 2022
First published
18 Jul 2022

Org. Chem. Front., 2022,9, 4699-4704

Synthesis of chiral β-substituted γ-amino-butyric acid derivatives via enantioconvergent ring opening of racemic 2-(hetero)aryl aziridines with ketene silyl acetals

L. Qi, P. Yang, W. Ji, G. Tao, G. Yang and Z. Chai, Org. Chem. Front., 2022, 9, 4699 DOI: 10.1039/D2QO00450J

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