Tandem of Asymmetric Organocatalysis and Selective Post-Functionalization: Enantiodivergent Synthesis of Bioactive Indane-1-Carboxylic Acid Derivatives

Tandem of Asymmetric Organocatalysis and Selective Post-Functionalization: Enantiodivergent Synthesis of Bioactive Indane-1-Carboxylic Acid Derivatives Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2025, Volume: 23, Number: 23, Pages: 5611-5615 Pages count : 5 DOI: 10.1039/d5ob00551e

Authors

Zhanabaeva Madina ^1,2 , Kovalevsky Ruslan A. ² , Kucherenko Alexander S. ² , Korlyukov Alexander A. ³ , Zlotin Sergei G. ²

Affiliations

1	D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., 125047, Moscow, Russian Federation
2	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, 119991, Moscow, Russian Federation
3	A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova, St., 119991 Moscow, Russian Federation

The first practical enantiodivergent synthesis of bioactive indane-1-carboxylic acid derivatives is developed. A key step of the synthesis is highly enantioselective organocatalytic Michael addition of allomaltol, an available natural kojic acid derivative, to 1H-inden-1-ones. Subsequent oxidative fragmentation of the reaction products under the action of RuCl3/NaIO4 followed by chemoselective reduction of the resulting ketoacids with zinc amalgam afforded indane-1-carboxylic acids of high enantiomeric purity unavailable so far. The synthetic potential of the method was demonstrated by a gram-scale synthesis of (S)- and (R)-enantiomers of anticoagulant camonagrel.

Zhanabaeva M. , Kovalevsky R.A. , Kucherenko A.S. , Korlyukov A.A. , Zlotin S.G.
Tandem of Asymmetric Organocatalysis and Selective Post-Functionalization: Enantiodivergent Synthesis of Bioactive Indane-1-Carboxylic Acid Derivatives
Organic & Biomolecular Chemistry. 2025. V.23. N23. P.5611-5615. DOI: 10.1039/d5ob00551e WOS Scopus OpenAlex

Web of science:	WOS:001490307900001
Scopus:	2-s2.0-105005761385
OpenAlex:	W4410168376

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