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Exo diastereoselective Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one

Journal Article


Abstract


  • The thermally induced Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one 2 and substituted 1,3-cyclohexadienes and substituted 1,3-butadienes gives exo diastereomeric Diels-Alder adducts. In some cases the initially formed adducts undergo epimerization at the amino-acetal carbon, however the stereochemical integrity of the quaternary α-amino acid stereogenic centre is maintained and Diels-Alder adducts can be obtained in high enantiomeric purity (> 90% ee). The stereochemistry of these adducts has been elucidated by single crystal X-ray structure determinations and 2D 1H NMR analysis. © 1994.

Publication Date


  • 1994

Citation


  • Pyne, S. G., Safaei-G, J., Hockless, D. C. R., Skelton, B. W., Sobolev, A. N., & White, A. H. (1994). Exo diastereoselective Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one. Tetrahedron, 50(3), 941-956. doi:10.1016/S0040-4020(01)80808-5

Scopus Eid


  • 2-s2.0-0028144422

Web Of Science Accession Number


Start Page


  • 941

End Page


  • 956

Volume


  • 50

Issue


  • 3

Abstract


  • The thermally induced Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one 2 and substituted 1,3-cyclohexadienes and substituted 1,3-butadienes gives exo diastereomeric Diels-Alder adducts. In some cases the initially formed adducts undergo epimerization at the amino-acetal carbon, however the stereochemical integrity of the quaternary α-amino acid stereogenic centre is maintained and Diels-Alder adducts can be obtained in high enantiomeric purity (> 90% ee). The stereochemistry of these adducts has been elucidated by single crystal X-ray structure determinations and 2D 1H NMR analysis. © 1994.

Publication Date


  • 1994

Citation


  • Pyne, S. G., Safaei-G, J., Hockless, D. C. R., Skelton, B. W., Sobolev, A. N., & White, A. H. (1994). Exo diastereoselective Diels-Alder reactions of (R)-2-phenyl-4-methylene-oxazolidin-5-one. Tetrahedron, 50(3), 941-956. doi:10.1016/S0040-4020(01)80808-5

Scopus Eid


  • 2-s2.0-0028144422

Web Of Science Accession Number


Start Page


  • 941

End Page


  • 956

Volume


  • 50

Issue


  • 3