Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2008, Issue 2, Pages 277-284Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200700724
Keywords
methoxyallene; nitrone; 1,3-dipolar cycloaddition; Lewis acids; isoxazolidines
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The siteselectivity of cycloadditions of the D-glyceraldehyde-derived nitrone I and methoxyallene (2) is strongly influenced by Lewis acids. The uncatalyzed reaction results in the formation of isomeric isoxazolidines 3a-3d and 4a-4c, whereas in the presence of different Lewis acids exclusive formation of 4-methylene-substituted isoxazolidines 4a-4d is observed. Furthermore, the diastereofacial selectivity of the methoxyallene addition to nitrone I can be controlled, thus giving rise to both diastereomeric isoxazolidines 3,4'-anti-4 or 3,4'-syn-4, just by employing different Lewis acids. The redox ring-opening of isoxazolidines 4 using Murahashi's protocol yields a-methylene-beta-amino acid esters 5a,b and 7a,b. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
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