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Open AccessArticle

Stereoselective Synthesis and Investigation of Isopulegol-Based Chiral Ligands

1
Institute of Pharmaceutical Chemistry, University of Szeged, Interdisciplinary excellent center, H-6720 Szeged, Eötvös utca 6, Hungary
2
Stereochemistry Research Group of the Hungarian Academy of Sciences, H-6720 Szeged, Eötvös utca 6, Hungary
3
Department of Microbiology, University of Szeged, 6726 Szeged, Közép fasor 52, Hungary
4
Interdisciplinary Centre of Natural Products, University of Szeged, H-6720 Szeged, Eötvös utca 6, Hungary
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2019, 20(16), 4050; https://doi.org/10.3390/ijms20164050
Received: 16 July 2019 / Revised: 5 August 2019 / Accepted: 15 August 2019 / Published: 19 August 2019
A library of isopulegol-based bi-, tri- and tetrafunctional chiral ligands has been developed from commercially available (−)-isopulegol and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. Michael addition of primary amines towards α-methylene-γ-butyrolactone, followed by reduction, was accomplished to provide aminodiols in highly stereoselective transformations. Stereoselective epoxidation of (+)-neoisopulegol, derived from natural (−)-isopulegol, and subsequent oxirane ring opening with primary amines afforded aminodiols. The regioselective ring closure of N-substituted aminodiols with formaldehyde was also investigated. Hydroxylation of (+)-neoisopulegol resulted in diol, which was then transformed into aminotriols by aminolysis of its epoxides. Dihydroxylation of (+)-neoisopulegol or derivatives with OsO4/NMO gave neoisopulegol-based di-, tri- and tetraols in highly stereoselective reactions. The antimicrobial activity of aminodiol and aminotriol derivatives as well as di-, tri- and tetraols was also explored. In addition, structure–activity relationships were examined by assessing substituent effects on the aminodiol and aminotriol systems. View Full-Text
Keywords: aminodiols; aminotriols; diols; triols; tetraols; chiral catalysts; antimicrobial activity aminodiols; aminotriols; diols; triols; tetraols; chiral catalysts; antimicrobial activity
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MDPI and ACS Style

Le, T.M.; Szilasi, T.; Volford, B.; Szekeres, A.; Fülöp, F.; Szakonyi, Z. Stereoselective Synthesis and Investigation of Isopulegol-Based Chiral Ligands. Int. J. Mol. Sci. 2019, 20, 4050.

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