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

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 meth...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2022-11, Vol.58 (92), p.12827-12830
Hauptverfasser:	Kovalevsky, Ruslan A., Kucherenko, Alexander S., Zlotin, Sergei G.
Format:	Artikel
Sprache:	eng
Schlagworte:	Adducts Amino acids Enantiomers Esterification Optical properties Optical rotation
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creator	Kovalevsky, Ruslan A. Kucherenko, Alexander S. Zlotin, Sergei G.
description	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.
doi_str_mv	10.1039/d2cc04909k
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source	Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects	Adducts Amino acids Enantiomers Esterification Optical properties Optical rotation
title	Concise enantioselective synthesis of non-proteinogenic α-aminoacids via an organocatalytic Mannich-type reaction
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