Synthesis and stereochemical analysis of some norephedrine-derived isoxazolidines

Basem Moosa, Mohamed I.M. Wazeer, Mohammed B. Fettouhi, Shaikh A. AIi

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The diastereoselectivity in the cycloaddition reactions of several mono- and disubstituted alkenes with a (-)norephedrine-derived methylenenitrone has been investigated. The stereochemical analysis of the addition products (i.e., isoxazolidines) has been carried out by X-ray, NMR, and chemical conversions. The NMR spectra of the isoxazolidines at low temperatures indicated the presence of either a single or a predominant invertomer. The stereochemistry of the invertomers and nitrogen inversion barriers are determined using complete line-shape analysis and their dependence on solvent is discussed.

Original languageEnglish (US)
Pages (from-to)212-220
Number of pages9
JournalJournal of Physical Organic Chemistry
Volume22
Issue number3
DOIs
StatePublished - Jan 1 2009

Keywords

  • Asymmetric induction
  • Cycloaddition reactions
  • Inversion barriers
  • Invertomers
  • Isoxazoldines
  • Nitrogen inversion
  • Nitrone
  • Stereochemistry

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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