Document Detail


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.
MedLine Citation:
PMID:  15369354     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Ramón Gómez Arrayás; Lanny S Liebeskind
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  125     ISSN:  0002-7863     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2003 Jul 
Date Detail:
Created Date:  2004-09-16     Completed Date:  2004-11-10     Revised Date:  2008-01-17    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  9026-7     Citation Subset:  IM    
Affiliation:
Department of Chemistry, Emory University, 1515 Pierce Drive, Atlanta, GA 30322, USA.
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MeSH Terms
Descriptor/Qualifier:
Aza Compounds / chemical synthesis*
Bicyclo Compounds / chemical synthesis*
Cyclization
Molybdenum / chemistry*
Organometallic Compounds / chemistry
Pyrans / chemistry*
Pyridines / chemistry*
Stereoisomerism
Grant Support
ID/Acronym/Agency:
GM 43107/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
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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