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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

, ,  and *
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 Nitrones; lactones; 1; 3-dipolar cycloaddition; stereoselectivity; regioselectivity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Cacciarini, M.; Cordero, F.M.; Faggi, C.; Goti, A. Cycloaddition Reactions of C,N-Diphenylnitrone to Methylene-γ-butyrolactones. Molecules 2000, 5, 637-647.

AMA Style

Cacciarini M, Cordero FM, Faggi C, Goti A. Cycloaddition Reactions of C,N-Diphenylnitrone to Methylene-γ-butyrolactones. Molecules. 2000; 5(4):637-647.

Chicago/Turabian Style

Cacciarini, Martina; Cordero, Franca M.; Faggi, Cristina; Goti, Andrea. 2000. "Cycloaddition Reactions of C,N-Diphenylnitrone to Methylene-γ-butyrolactones." Molecules 5, no. 4: 637-647.



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