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

Molecules

Martina Cacciarini¹  Franca M. Cordero¹  Cristina Faggi¹ 

[1] 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

关键词: Nitrones;    lactones;    1;    3-dipolar cycloaddition;    stereoselectivity;    regioselectivity;   

DOI  :  10.3390/50400637

来源: mdpi

【 摘 要 】

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.

【 授权许可】

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