Issue 92, 2022

Concise enantioselective synthesis of non-proteinogenic α-aminoacids via an organocatalytic Mannich-type reaction

Abstract

A bifunctional tertiary amine-squaramide-catalyzed enantioselective Mannich-type addition of available allomaltol to N-protected aldimines was developed. The resulted adducts were readily transformed into non-proteinogenic α-amino acids and their derivatives were not easily accessible by other methods via oxidative fragmentation, esterification, amidation and deprotection reactions. The absolute (S)-configuration of the thus obtained α-amino acids was established by comparison of the N-Ts-PheGly optical rotation sign with the reported data.

Graphical abstract: Concise enantioselective synthesis of non-proteinogenic α-aminoacids via an organocatalytic Mannich-type reaction

Supplementary files

Article information

Article type
Communication
Submitted
05 Sep 2022
Accepted
24 Oct 2022
First published
24 Oct 2022

Chem. Commun., 2022,58, 12827-12830

Concise enantioselective synthesis of non-proteinogenic α-aminoacids via an organocatalytic Mannich-type reaction

R. A. Kovalevsky, A. S. Kucherenko and S. G. Zlotin, Chem. Commun., 2022, 58, 12827 DOI: 10.1039/D2CC04909K

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