| Synthesis of enantiopure trans-N-Boc-3-aminobicyclo[2.2.2]octane-2-carboxylic acids and their bicyclic 1,3-amino alcohol derivatives via the [4+2] cycloaddition of 1,3-cyclohexadiene to a chiral β-nitroacrylate. | |
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MedLine Citation:
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PMID: 20928894 Owner: NLM Status: In-Data-Review |
Abstract/OtherAbstract:
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The chiral β-nitroacrylate 2 derived from the (R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid 1 acts as a reactive dienophile in a diastereoselective Diels-Alder reaction with 1,3-cyclohexadiene. The major cycloadducts have been isolated and transformed into enantiopure trans(2S,3S)- or (2R,3R)-N-Boc-3-aminobicyclic[2,2,2]octane-2-carboxylic acids 5. The trans-(2S,3S)- or (2R,3R)-N-Boc 3-(hydoxymethyl)-2-aminobicyclic[2,2,2]octane 6 derivatives were also obtained. Chirality, 2011. © 2010 Wiley-Liss, Inc. |
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Authors:
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Monique Calmes; Françoise Escale; Claude Didierjean; Jean Martinez |
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Publication Detail:
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Type: Journal Article Date: 2010-10-06 |
Journal Detail:
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Title: Chirality Volume: 23 ISSN: 1520-636X ISO Abbreviation: Chirality Publication Date: 2011 Mar |
Date Detail:
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Created Date: 2011-02-09 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 8914261 Medline TA: Chirality Country: United States |
Other Details:
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Languages: eng Pagination: 245-9 Citation Subset: IM |
Copyright Information:
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Copyright © 2010 Wiley-Liss, Inc. |
Affiliation:
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Institut des Biomolécules Max Mousseron (IBMM) UMR 5247 CNRS-UM1-UM2, Université Montpellier 2, Bâtiment Chimie (17), 34095 Montpellier cedex 5, France. monique.calmes@univ-montp2.fr. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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