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Note | Regular issue | Vol 65, No. 6, 2005, pp.1447-1454
Published online, 8th April, 2005
DOI: 10.3987/COM-05-10376
Spiroaziridines from 4-Substituted α-Ylidene-γ-butyro Lactones

Tecla Gasperi, M. Antonietta Loreto,* Antonella Migliorini, and Paolo A. Tardella

*Dipartimento di Chimica, Università degli Studi di Roma “La Sapienza”, P. le A. Moro 5, 00185 Rome, Italy

Abstract

4-Substituted α-ylidene-γ-butyrolactones produce N-ethoxycarbonylspiroaziridino γ-lactone diastereomers on treatment with NsONHCO2Et and CaO. A good stereofacial preference is observed when the ring substituent is a phenyl group. These products are precursors of α-aminolactone as pure diastereomers.