Document Detail


Control of diastereoselectivity for iridium-catalyzed allylation of a prochiral nucleophile with a phosphate counterion.
MedLine Citation:
PMID:  23286279     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
We report a highly diastereo- and enantioselective allylation of azlactones catalyzed by the combination of a metallacyclic iridium complex and an optically inactive phosphate anion. The process demonstrates an approach for conducting diastereoselective reactions with prochiral nucleophiles in the presence of metallacyclic allyliridium complexes. The reaction provides access to an array of enantioenriched allylated azlactones containing adjacent tertiary and quaternary carbon centers. Preliminary mechanistic studies suggest that the phosphate and methyl carbonate anions together induce the unusually high diastereoselectivity.
Authors:
Wenyong Chen; John F Hartwig
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2013-01-30
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  135     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2013 Feb 
Date Detail:
Created Date:  2013-02-13     Completed Date:  2013-08-01     Revised Date:  2014-02-14    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  2068-71     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Alkylation
Allyl Compounds / chemical synthesis*,  chemistry
Catalysis
Iridium / chemistry*
Lactones / chemistry*
Molecular Structure
Organometallic Compounds / chemistry*
Phosphates / chemistry*
Stereoisomerism
Grant Support
ID/Acronym/Agency:
GM-58108/GM/NIGMS NIH HHS; R01 GM058108/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Allyl Compounds; 0/Lactones; 0/Organometallic Compounds; 0/Phosphates; 44448S9773/Iridium
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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