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Communication | Special issue | Vol 40, No. 1, 1995, pp.97-100
Published online, 1st January, 1970
DOI: 10.3987/COM-94-S17
Unexpected Stereoselectivity of Intramolecular 1,3-Dipolar Cycloaddition Caused by the Presence of Fluorine Atom

Masataka Ihara, Tatsuo Kawabuchi, Yuji Tokunaga, and Keiichiro Fukumoto

*Pharnaceutical Institute, Tohoku University, Aramaki, Aoba-ku, sendai 980-8578, Japan


Intramolecular 1,3-dipolar cycloaddition of nitrones (11; R = Me, Et, and Bn) bearing one fluorine atom at the quaternary α-position produced two diastereoisomers of bicyclic isoxazolidines (12) and (13). It was revealed that the stereochemical outcome was considerably influenced by the presence of fluorine atom.