Journal
TETRAHEDRON-ASYMMETRY
Volume 19, Issue 19, Pages 2246-2251Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2008.09.016
Keywords
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Funding
- Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi
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The stereoselective synthesis of oxaziridines with three stereogenic centres is presented in this paper. The chirality is provided by asymmetric induction, and a possible mechanism for the induced stereoselectivity is also discussed. These small heterocycles undergo the [3+2] cycloaddition reaction with aryl ethenes to afford enantiomerically pure isoxazolidines of controlled configurations. This class of heterocycles is present in the structure of various compounds of biological and pharmacological interest, which can undergo further synthetic modifications. (C) 2008 Elsevier Ltd. All rights reserved.
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