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

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

Journal

Chemical Communications
ISSN: 1359-7345 , E-ISSN: 1364-548X

Output data

Year: 2022, Volume: 58, Number: 92, Pages: 12827-12830 Pages count : 4 DOI: 10.1039/d2cc04909k

Authors

Kovalevsky Ruslan A. ^1,2 , Kucherenko Alexander S. ¹ , Zlotin Sergei G. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, Russian Federation
2	M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie gory 1-3, Moscow, Russian Federation

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.

Kovalevsky R.A. , Kucherenko A.S. , Zlotin S.G.
Concise enantioselective synthesis of non-proteinogenic α-aminoacids via an organocatalytic Mannich-type reaction
Chemical Communications. 2022. V.58. N92. P.12827-12830. DOI: 10.1039/d2cc04909k WOS Scopus OpenAlex

Web of science:	WOS:000876550700001
Scopus:	2-s2.0-85141787498
OpenAlex:	W4307771475

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