Stereoselective synthesis and investigation of isopulegol-based chiral ligands

Tam Minh Le, Tamás Szilasi, Bettina Volford, András Szekeres, Ferenc Fülöp, Zsolt Szakonyi

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3 Citations (Scopus)

Abstract

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 a-methylene-?- 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.

Original languageEnglish
Article number4050
JournalInternational journal of molecular sciences
Volume20
Issue number16
DOIs
Publication statusPublished - Aug 2 2019

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Keywords

  • Aminodiols
  • Aminotriols
  • Antimicrobial activity
  • Chiral catalysts
  • Diols
  • Tetraols
  • Triols

ASJC Scopus subject areas

  • Catalysis
  • Molecular Biology
  • Spectroscopy
  • Computer Science Applications
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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