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Beilstein J Org Chem. 2012;8:100-6. doi: 10.3762/bjoc.8.10. Epub 2012 Jan 17.

Synthesis of highly functionalized β-aminocyclopentanecarboxylate stereoisomers by reductive ring opening reaction of isoxazolines.

Author information

  • 1Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary.

Abstract

A rapid and simple procedure was devised for the synthesis of multifunctionalized cyclic β-amino esters and γ-amino alcohols via the 1,3-dipolar cycloaddition of nitrile oxides to β-aminocyclopentenecarboxylates. The opening of the isoxazoline reductive ring to the corresponding highly functionalized 2-aminocyclopentanecarboxylates occurred stereoselectively with good yields.

KEYWORDS:

amino acids; cycloaddition; functionalization; isoxazolines; reduction

PMID:
22423276
[PubMed]
PMCID:
PMC3302068
Free PMC Article
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