| N-benzyl aspartate nitrones: unprecedented single-step synthesis and [3 + 2] cycloaddition reactions with alkenes. | |
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MedLine Citation:
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PMID: 18785749 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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N-benzyl aspartate nitrones 2, prepared by addition of N-benzylhydroxylamine to dialkyl acetylenedicarboxylates 1, underwent [3 + 2] thermal cycloaddition with a wide range of alkenes to afford isoxazolidines 4 bearing a polyfunctionalized quaternary center. Under these uncatalyzed conditions, the trans stereocontrol observed with vinyl ethers is higher than that obtained with all acyclic activated nitrones reported to date. The first asymmetric access to a type-4 pure adduct was achieved starting from the chiral aspartate nitrone derived from (S)-alpha-methylbenzylhydroxylamine. |
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Authors:
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Thanh Binh Nguyen; Arnaud Martel; Robert Dhal; Gilles Dujardin |
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Publication Detail:
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Type: Journal Article Date: 2008-09-12 |
Journal Detail:
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Title: Organic letters Volume: 10 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2008 Oct |
Date Detail:
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Created Date: 2008-10-09 Completed Date: 2008-12-10 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 4493-6 Citation Subset: - |
Affiliation:
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UCO2M UMR 6011 & IRIM2F FR 2575 CNRS, Université du Maine, 72085, Le Mans, France. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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