| Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor. | |
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MedLine Citation:
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PMID: 22543734 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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The first enantioselective synthesis of a potent GlyT1 inhibitor is described. A 3-nitroazetidine donor is used in an enantioselective aza-Henry reaction catalyzed by a bis(amidine)-triflic acid salt organocatalyst, delivering the key intermediate with 92% ee. This adduct is reductively denitrated and converted to the target through a short sequence, thereby allowing assignment of the absolute configuration of the more potent enantiomer. |
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Authors:
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Tyler A Davis; Michael W Danneman; Jeffrey N Johnston |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-4-30 |
Journal Detail:
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Title: Chemical communications (Cambridge, England) Volume: - ISSN: 1364-548X ISO Abbreviation: - Publication Date: 2012 Apr |
Date Detail:
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Created Date: 2012-4-30 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9610838 Medline TA: Chem Commun (Camb) Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Department of Chemistry & Vanderbilt Institute of Chemical Biology Vanderbilt University, Nashville, TN 37235-1822, USA. jeffrey.n.johnston@vanderbilt.edu. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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