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Two isoxazolidines

S Niwayama1, Y You, K N Houk

  • 1Department of Chemistry and Biochemistry, University of California, Los Angeles 90024-1569, USA. khan/chem.ucla.edu

Acta Crystallographica. Section C, Crystal Structure Communications
|February 15, 1996
PubMed
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This study reports the crystal structures of two novel spirocyclic compounds. The research also investigated the stereoselectivity of cycloaddition reactions involving isoxazolidine derivatives.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Stereochemistry

Background:

  • Isoxazolidine rings are five-membered heterocycles containing adjacent nitrogen and oxygen atoms.
  • Spirocyclic compounds feature two rings sharing a single common atom.
  • 1,3-Dipolar cycloaddition is a fundamental reaction in organic synthesis for forming five-membered rings.

Purpose of the Study:

  • To determine the crystal structures of two novel phenyl ketone substituted spirocyclic compounds.
  • To elucidate the conformational preferences of the isoxazolidine rings within these spirocyclic systems.
  • To investigate the stereochemical outcome (endo selectivity) of 1,3-dipolar cycloaddition reactions.

Main Methods:

  • X-ray crystallography was employed to determine the three-dimensional structures of the synthesized compounds.

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  • Spectroscopic techniques were likely used for compound characterization (though not explicitly stated in the abstract).
  • Analysis of reaction products from 1,3-dipolar cycloadditions to assess stereoselectivity.

    • Main Results:

    • The crystal structures of trans-phenyl-1,6-dioxa-2-azaspiro[4,4]non-3-yl ketone and (3 alpha,3a alpha,6a alpha)-hexahydro-2-phenylfuro[3,2-d]isoxazol-3-yl phenyl ketone were determined.
    • In both determined structures, the isoxazolidine rings adopt an envelope conformation.
    • The O atom in the isoxazolidine ring was observed to be significantly displaced from the plane formed by the other four ring atoms.
    • 1,3-Dipolar cycloaddition reactions exhibited modest to negligible endo selectivity.

    Conclusions:

    • The conformational analysis of the isoxazolidine rings provides insights into their three-dimensional geometry.
    • The observed envelope conformation influences the reactivity and stereochemical outcome of cycloaddition reactions.
    • The study contributes to understanding the synthesis and structural properties of spirocyclic isoxazolidine derivatives.