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Synlett 1997; 1997(1): 100-102
DOI: 10.1055/s-1997-683
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Diastereoselective Michael Reactions of Azomethine Ylides to Chiral 4-Methyleneoxazolidin-5-ones: Synthesis of the Four Stereoisomers of 4-Benzamindopyroglutamate

Abdollah Javindan, Karl Schafer, Stephen G. Pyne*
  • *Department of Chemistry, University of Wollongong, Wollongong, NSW, 2522, Australia, Fax +61-42-214287; e-mail: S.Pyne@uow.edu.au
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Publication Date:
22 March 2004 (online)

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The diastereoselective Michael addition reactions of the azomethine ylides derived from the α-(alkylideneamino) esters 2,3 and 17 with the chiral oxazolidinones 1 and 8 allow for a practical synthesis of all four stereoisomers of 4-benzamidopyroglutamate.

Michael reaction - azomethine ylides - pyroglutamate - oxazolidinone

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