Diastereoselective synthesis of novel optically active five membered O-and N-heterocyclic compounds

Ervin Kovács, Ferenc Farkas, Angelika Thurner, A. Szöllösy, F. Faigl

Research output: Contribution to journalArticle

Abstract

Optically active oxetane and cis-but-2-ene-1,4-diol derivatives were used as starting materials in the synthesis of novel five membered heteorcyclic compounds as dihydrofuran and pyrroline derivatives. In addition, new 2,4-disubstituted dioxolane was synthesized diastereoselectively from the diol and the structure of the product was confirmed by NOESY (Nuclear Overhauser Effect Spectroscopy) experiments. Reductive ring opening of the chiral oxetane derivative provided a 3,4-disubstituted-butane-1,4-diol which was used for the synthesis of new chiral pyrrolidine and tetrahydrofuran derivatives.

Original languageEnglish
Pages (from-to)81-88
Number of pages8
JournalLetters in Organic Chemistry
Volume9
Issue number2
DOIs
Publication statusPublished - Feb 2012

Fingerprint

Heterocyclic Compounds
Derivatives
Spectrum Analysis
Spectroscopy
oxetane
Experiments
formal glycol
tetrahydrofuran
1-butene
butane
pyrroline
pyrrolidine

Keywords

  • Diastereoselective dioxolane synthesis
  • Dihydrofuran
  • Enantioselective reactions
  • NOESY experiments
  • Pyrrolidine
  • Pyrroline
  • Tetrahydrofuran

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry

Cite this

Diastereoselective synthesis of novel optically active five membered O-and N-heterocyclic compounds. / Kovács, Ervin; Farkas, Ferenc; Thurner, Angelika; Szöllösy, A.; Faigl, F.

In: Letters in Organic Chemistry, Vol. 9, No. 2, 02.2012, p. 81-88.

Research output: Contribution to journalArticle

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