Synthesis of chiral 1,5-disubstituted pyrrolidinones via electrophile-induced cyclization of 2-(3-butenyl)oxazolines derived from (1R,2S)- and (1S,2R)-norephedrine

Iván Kanizsai, Z. Szakonyi, Reijo Sillanpää, Matthias D'hooghe, Norbert De Kimpe, F. Fülöp

Research output: Contribution to journalArticle

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Abstract

Starting from (1R,2S)- and (1S,2R)-norephedrine, enantiomers of the corresponding 2-(3-butenyl)oxazolines were prepared in a two-step process. The cyclization of the intermediate alkenylamides with phenylselenyl bromide afforded cyclic imidates instead of the expected pyrrolidinones. The electrophile-induced cyclizations of 2-alkenyloxazolines with bromine or iodine produced diastereomeric mixtures of chiral 1,5-disubstituted pyrrolidinones. The ring closure of the all-cis (1R,2S,5R)-diastereomer 7 with NaH resulted in the tetrahydropyrrolo[2,1-b]oxazol-5-one derivative 18, which was alternatively prepared by the cyclocondensation of (1R,2S)-norephedrine with levulinic acid.

Original languageEnglish
Pages (from-to)2857-2863
Number of pages7
JournalTetrahedron Asymmetry
Volume17
Issue number20
DOIs
Publication statusPublished - Nov 6 2006

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Phenylpropanolamine
Pyrrolidinones
Cyclization
enantiomers
bromine
closures
iodine
bromides
Imidoesters
Bromine
acids
Enantiomers
rings
synthesis
Iodine
Bromides
Derivatives
Acids
levulinic acid

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Synthesis of chiral 1,5-disubstituted pyrrolidinones via electrophile-induced cyclization of 2-(3-butenyl)oxazolines derived from (1R,2S)- and (1S,2R)-norephedrine. / Kanizsai, Iván; Szakonyi, Z.; Sillanpää, Reijo; D'hooghe, Matthias; Kimpe, Norbert De; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 17, No. 20, 06.11.2006, p. 2857-2863.

Research output: Contribution to journalArticle

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