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Note | Special issue | Vol 67, No. 1, 2006, pp.413-420
Published online, 13th September, 2005
DOI: 10.3987/COM-05-S(T)37
1,3-Dipolar Cycloadditions of 2-tert-Butoxycarbonyl-1-pyrroline N-Oxide with Chiral Acrylates and Acrylamides

Federica Pisaneschi, Martina Gensini, Maria Salvati, Franca M. Cordero, and Alberto Brandi*

*Dipartimento di Chimica Organica “Ugo Schiff”, Università di Firenze, Via della Lastruccia n. 3, I-50019 Sesto Fiorentino (Fi), Italy

Abstract

The 1,3-dipolar cycloadditions of a series of chiral acrylates and acrylamides with 2-tert-butoxycarbonyl-1-pyrroline N-oxide were studied. The synthesis of enantiopure tert-butyl (2R,7aR)- and (2S,7aS)-2-hydroxy-3-oxo-tetrahydro-1H-pyrrolizine-7a(5H)-carboxylates starting from the acryloyloxazolidinone derived from (S)-phenylalanine is reported.