| Eta3-pyranyl and eta3-pyridinyl molybdenum pi-complexes as chiral scaffolds for the enantioselective construction of substituted oxa- and aza[3.3.1]bicyclics: first enantio- and regiocontrolled [5+3] cycloaddition reactions. | |
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MedLine Citation:
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PMID: 15369354 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The first Mo-mediated [5+3] cycloadditions are reported. 3-Substituted pyranyl and pyridinyl molybdenum pi-complexes participate in enantiocontrolled [5+3] cycloadditions and provide a new and efficient synthetic approach to oxa- and aza[3.3.1]bicyclics of high enantiomeric purity. The reaction proceeds in good to excellent yields and with complete regio- and endo-selectivities; it diverts to a [2+3] cycloaddition pathway when 2-substituted heterocycle pi-complexes are used. This methodology, coupled with a variety of general demetalation protocols, holds much promise in synthetic applications. |
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Authors:
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Ramón Gómez Arrayás; Lanny S Liebeskind |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 125 ISSN: 0002-7863 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2003 Jul |
Date Detail:
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Created Date: 2004-09-16 Completed Date: 2004-11-10 Revised Date: 2008-01-17 |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 9026-7 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, GA 30322, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Aza Compounds
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chemical synthesis* Bicyclo Compounds / chemical synthesis* Cyclization Molybdenum / chemistry* Organometallic Compounds / chemistry Pyrans / chemistry* Pyridines / chemistry* Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM 43107/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Aza Compounds; 0/Bicyclo Compounds; 0/Organometallic Compounds; 0/Pyrans; 0/Pyridines; 7439-98-7/Molybdenum |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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