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Asymmetric synthesis of chiral cyclic amino acids by diels-alder reactions of (2s)- and (2r)-4-methyleneoxazolidin-5-ones

Journal Article


Abstract


  • The synthesis of chiral (2S)- and (2R)-4-methyleneoxazolidin-5-ones, in high enantiomeric purity from (S)-S- methylcysteine, and their highly exo-selective Diels -Alder reactions with cyclic dienes are described. (1R, 2S, 4S)-2-Aminobicyclo[2.2.1]heptane-2-carboxylic acid has been prepared in 92% e.e. by these methods. A number of the products have been characterized by single-crystal X-ray methods, and their structure systematics examined. © 1993 ASEG.

Publication Date


  • 1993

Citation


  • Pyne, S. G., Dikic, B., & Gordon, P. A. (1993). Asymmetric synthesis of chiral cyclic amino acids by diels-alder reactions of (2s)- and (2r)-4-methyleneoxazolidin-5-ones. Australian Journal of Chemistry, 46(1), 73-93. doi:10.1071/CH9930073

Scopus Eid


  • 2-s2.0-84913968196

Web Of Science Accession Number


Start Page


  • 73

End Page


  • 93

Volume


  • 46

Issue


  • 1

Abstract


  • The synthesis of chiral (2S)- and (2R)-4-methyleneoxazolidin-5-ones, in high enantiomeric purity from (S)-S- methylcysteine, and their highly exo-selective Diels -Alder reactions with cyclic dienes are described. (1R, 2S, 4S)-2-Aminobicyclo[2.2.1]heptane-2-carboxylic acid has been prepared in 92% e.e. by these methods. A number of the products have been characterized by single-crystal X-ray methods, and their structure systematics examined. © 1993 ASEG.

Publication Date


  • 1993

Citation


  • Pyne, S. G., Dikic, B., & Gordon, P. A. (1993). Asymmetric synthesis of chiral cyclic amino acids by diels-alder reactions of (2s)- and (2r)-4-methyleneoxazolidin-5-ones. Australian Journal of Chemistry, 46(1), 73-93. doi:10.1071/CH9930073

Scopus Eid


  • 2-s2.0-84913968196

Web Of Science Accession Number


Start Page


  • 73

End Page


  • 93

Volume


  • 46

Issue


  • 1