Document Detail


Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones.
MedLine Citation:
PMID:  21815666     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A chiral Brønsted acid has been developed from a cationic gold(I) disphosphine complex in the presence of alcoholic solvent and applied to the enantioselective protonation reaction of silyl enol ethers of ketones. Various optically active cyclic ketones were obtained in excellent yields and high enantioselectivities, including cyclic ketones bearing aliphatic substrates at the α-position. Furthermore, the application of this Brønsted acid was extended to the first Brønsted acid-catalyzed enantioselective protonation reaction of silyl enol ethers of acyclic substrates, regardless of their E/Z ratio.
Authors:
Cheol Hong Cheon; Osamu Kanno; F Dean Toste
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2011-08-04
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  133     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2011 Aug 
Date Detail:
Created Date:  2011-08-24     Completed Date:  2011-12-20     Revised Date:  2014-09-17    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  13248-51     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Acids / chemistry*
Catalysis
Cations / chemistry
Ethers / chemistry
Ketones / chemistry
Organogold Compounds / chemistry*
Phosphines / chemistry*
Stereoisomerism
Grant Support
ID/Acronym/Agency:
R01 GM073932/GM/NIGMS NIH HHS; R01 GM073932/GM/NIGMS NIH HHS; R01 GM073932-06/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Acids; 0/Cations; 0/Ethers; 0/Ketones; 0/Organogold Compounds; 0/Phosphines
Comments/Corrections

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