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• Cacciarini, M
• Cordero, FM.
• Faggi, C
• Goti, A
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• Cacciarini, M
• Cordero, FM.
• Faggi, C
• Goti, A
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• Cacciarini, M
• Cordero, FM.
• Faggi, C
• Goti, A

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Molecules 2000, 5(4), 637-647; doi:10.3390/50400637

Article

Cycloaddition Reactions of C,N-Diphenylnitrone to Methylene-γ-butyrolactones

Martina Cacciarini, Franca M. Cordero, Cristina Faggi and Andrea Goti*

Dipartimento di Chimica Organica "Ugo Schiff", Centro di studio sulla Chimica e la Struttura dei Composti Eterociclici e loro Applicazioni (CSCEA) C. N. R., Università di Firenze, via G. Capponi 9, I-50121 Firenze, Italy

* Author to whom correspondence should be addressed.

Received: 6 March 2000 / Accepted: 21 March 2000 / Published: 2 April 2000

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Abstract: Cycloaddition of C,N-diphenylnitrone to α-methylene-γ-butyrolactone afforded two diastereomeric 5-spirosubstituted isoxazolidines with high selectivity. Structural assignment was ascertained by NMR studies and an X-ray diffraction experiment on a single crystal of the major isomer and the diastereoselectivity was rationalized on examination of the alternative transition states leading to the two diastereoisomers.

Keywords: Nitrones; lactones; 1; 3-dipolar cycloaddition; stereoselectivity; regioselectivity

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