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Scientific article
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Iron and Ruthenium Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions between Nitrones and Enals

Published inJournal of the American Chemical Society, vol. 124, p. 4968-4969
Publication date2002
Abstract

The single coordination-site transition metal Lewis acids [CpM(BIPHOP-F)][SbF6] (M = Fe, Ru) catalyze the [3+2] dipolar cycloaddition reaction between reactive nitrones and a,ß-unsaturated aldehydes to give chiral isoxazolidines with ee values of 75 to >96%. The stereochemistry of the major enantiomer is consistent with an endo approach of the nitrone to the Ca-Si-face of the enal in the s-trans conformation in the (R,R)-catalyst site. The absolute configuration is based on an X-ray structure determination.

Citation (ISO format)
VITON, Florian, BERNARDINELLI, Gérald Hugues, KUNDIG, Ernst Peter. Iron and Ruthenium Lewis Acid Catalyzed Asymmetric 1,3-Dipolar Cycloaddition Reactions between Nitrones and Enals. In: Journal of the American Chemical Society, 2002, vol. 124, p. 4968–4969. doi: 10.1021/ja017814f
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