Asymmetric Synthesis of Functionalized α-Amino Acid Derivatives via the γ-Pyrone Carbaldimine-Based Organocatalytic Mannich Reaction

Asymmetric Synthesis of Functionalized α-Amino Acid Derivatives via the γ-Pyrone Carbaldimine-Based Organocatalytic Mannich Reaction Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2024, Volume: 89, Number: 16, Pages: 11357-11370 Pages count : 14 DOI: 10.1021/acs.joc.4c01037

Authors

Smirnov Maxim V. ^1,2 , Zhanabaeva Madina ^3,2 , Kucherenko Alexander S. ² , Kuznetsova Olga Yu. ² , Zlotin Sergei G. ²

Affiliations

1	Moscow State University, Department of Chemistry, Leninskie gory, 1-3, Moscow 119234, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect, 47, Moscow 119991, Russian Federation
3	D. Mendeleev University of Chemical Technology of Russia, Miusskaya Sq., 9, Moscow 125047, Russian Federation

A powerful synthetic strategy for the asymmetric synthesis of enantiomerically enriched γ-functionalized α-amino acid derivatives based on the highly stereoselective proline-catalyzed Mannich-type reaction of pre-prepared or in situ-generated γ-pyrone-derived aldimines with carbonyl compounds and subsequent transformations of multifunctional reaction products has been developed. A significant positive nonlinear effect was detected for the key organocatalytic reaction. The developed strategy was applied for facile gram-scale preparation of (S)-γ-oxonorvaline, used for site-specific modification of proteins, and both enantiomers of amycolatolide A recently isolated from the lichen-derived actinomycete Amycolatopsis sp. YIM 130923.

Smirnov M.V. , Zhanabaeva M. , Kucherenko A.S. , Kuznetsova O.Y. , Zlotin S.G.
Asymmetric Synthesis of Functionalized α-Amino Acid Derivatives via the γ-Pyrone Carbaldimine-Based Organocatalytic Mannich Reaction
Journal of Organic Chemistry. 2024. V.89. N16. P.11357-11370. DOI: 10.1021/acs.joc.4c01037 WOS Scopus OpenAlex

Web of science:	WOS:001282039000001
Scopus:	2-s2.0-85200346388
OpenAlex:	W4401200619

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OpenAlex	3
Scopus	2
Web of science	2