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Electronic effects in 1,3-dipolar cycloaddition reactions of N-alkyl and N-benzyl nitrones with dipolarophiles

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Published in Organic and Biomolecular Chemistry. 2012, vol. 10, no. 1, p. 114
Abstract 1,3-Dipolar cycloadditions afforded fast access to isoxazolidines bearing N-alkyl or N-benzyl substituents. The electronic properties of the substituents in the nitrones define the activity of the dipoles and modulate diastereoselectivity in the non-catalyzed reactions. Using a chiral one-point binding ruthenium Lewis acid catalyst, products were obtained in good yields and with excellent regio-, diastereo-, and enantioselectivity.
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Other version: http://xlink.rsc.org/?DOI=c1ob06144e
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BADOIU, Andréi, KUNDIG, Ernst Peter. Electronic effects in 1,3-dipolar cycloaddition reactions of N-alkyl and N-benzyl nitrones with dipolarophiles. In: Organic and Biomolecular Chemistry, 2012, vol. 10, n° 1, p. 114. https://archive-ouverte.unige.ch/unige:17734

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Deposited on : 2011-12-06

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