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1, 3-Dipolar Cycloadditions of a Chiral Oxazolidinone With Nitrones and Nitrile Oxides

Journal Article


Abstract


  • The 1, 3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5, 5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered π-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a, b) had the expected stereochemistry, addition of the 1, 3-dipole having occurred from the less hindered π-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations. © 1995 ASEG.

Publication Date


  • 1995

Citation


  • Pyne, S. G., & Safaei-G, J. (1995). 1, 3-Dipolar Cycloadditions of a Chiral Oxazolidinone With Nitrones and Nitrile Oxides. Australian Journal of Chemistry, 48(9), 1511-1533. doi:10.1071/CH9951511

Scopus Eid


  • 2-s2.0-84970571271

Web Of Science Accession Number


Start Page


  • 1511

End Page


  • 1533

Volume


  • 48

Issue


  • 9

Abstract


  • The 1, 3-dipolar cycloaddition reactions of the chiral oxazolidinone (1) and nitrones are highly regioselective and only 5, 5-disubstituted isoxazolidine adducts are formed. These reactions occur under equilibrating conditions to give the more stable adducts that result from addition to the exocyclic methylene of (1) from the sterically more hindered π-face. The endo adducts are generally thermodynamically favoured. In one case the novel azetidine (21) was formed from the treatment of the adduct (4a) with palladium hydroxide on carbon under a hydrogen atmosphere. The major adducts from the reaction of (1) and nitrile oxides (16a, b) had the expected stereochemistry, addition of the 1, 3-dipole having occurred from the less hindered π-face of the exocyclic methylene of (1). The stereochemistry of many of these products has been elucidated by single-crystal X-ray structural determinations. © 1995 ASEG.

Publication Date


  • 1995

Citation


  • Pyne, S. G., & Safaei-G, J. (1995). 1, 3-Dipolar Cycloadditions of a Chiral Oxazolidinone With Nitrones and Nitrile Oxides. Australian Journal of Chemistry, 48(9), 1511-1533. doi:10.1071/CH9951511

Scopus Eid


  • 2-s2.0-84970571271

Web Of Science Accession Number


Start Page


  • 1511

End Page


  • 1533

Volume


  • 48

Issue


  • 9