Synthesis and application of 1,2-aminoalcohols with neoisopulegol-based octahydrobenzofuran core

Fatima Zahra Bamou, Tam Minh Le, Bettina Volford, András Szekeres, Zsolt Szakonyi

Research output: Contribution to journalArticle

Abstract

A library of 1,2-aminoalcohol derivatives with a neoisopulegol-based octahydrobenzofuran core was developed and applied as chiral catalysts in the addition of diethylzinc to benzaldehyde. The allylic chlorination of (+)-neoisopulegol, derived from natural (-)-isopulegol followed by cyclization, gave the key methyleneoctahydrobenzofuran intermediate. The stereoselective epoxidation of the key intermediate and subsequent oxirane ring opening with primary amines afforded the required 1,2-aminoalcohols. The ring closure of the secondary amine analogues with formaldehyde provided spiro-oxazolidine ring systems. The dihydroxylation of the methylenetetrahydrofuran moiety with OsO4/NMO (4-methylmorpholine N-oxide) resulted in the formation of a neoisopulegol-based diol in a highly stereoselective reaction. The antimicrobial activity of both the aminoalcohol derivatives and the diol was also explored.

Original languageEnglish
Article number21
JournalMolecules
Volume25
Issue number1
DOIs
Publication statusPublished - Jan 1 2020

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Amines
Derivatives
Ethylene Oxide
Epoxidation
Chlorination
Halogenation
rings
Cyclization
amines
synthesis
Formaldehyde
Libraries
chlorination
epoxidation
formaldehyde
Catalysts
closures
analogs
catalysts
oxides

Keywords

  • 1 2-aminoalcohol
  • Antimicrobial activity
  • Chiral catalyst
  • Neoisopulegol
  • Octahydrobenzofuran

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis and application of 1,2-aminoalcohols with neoisopulegol-based octahydrobenzofuran core. / Bamou, Fatima Zahra; Le, Tam Minh; Volford, Bettina; Szekeres, András; Szakonyi, Zsolt.

In: Molecules, Vol. 25, No. 1, 21, 01.01.2020.

Research output: Contribution to journalArticle

Bamou, Fatima Zahra ; Le, Tam Minh ; Volford, Bettina ; Szekeres, András ; Szakonyi, Zsolt. / Synthesis and application of 1,2-aminoalcohols with neoisopulegol-based octahydrobenzofuran core. In: Molecules. 2020 ; Vol. 25, No. 1.
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