Document Detail


Achiral counterion control of enantioselectivity in a Brønsted acid-catalyzed iodolactonization.
MedLine Citation:
PMID:  22463391     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Highly enantioselective halolactonizations have been developed that employ a chiral proton catalyst-N-iodosuccinimide (NIS) reagent system in which the Brønsted acid is used at catalyst loadings as low as 1 mol %. An approach that modulates the achiral counterion (equimolar to the neutral chiral ligand-proton complex present at low catalyst loadings) to optimize the enantioselection is documented for the first time in this transformation. In this way, unsaturated carboxylic acids are converted to γ-lactones in high yields (up to 98% ee) using commercially available NIS.
Authors:
Mark C Dobish; Jeffrey N Johnston
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2012-03-30
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  134     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2012 Apr 
Date Detail:
Created Date:  2012-04-11     Completed Date:  2012-08-16     Revised Date:  2013-06-26    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6068-71     Citation Subset:  IM    
Copyright Information:
© 2012 American Chemical Society
Affiliation:
Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235, USA.
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MeSH Terms
Descriptor/Qualifier:
Carboxylic Acids / chemistry
Catalysis
Halogens
Hexanes / chemistry
Hydrogen Bonding
Ions*
Ligands
Models, Chemical
Stereoisomerism
Succinimides / chemistry
Temperature
Grant Support
ID/Acronym/Agency:
GM084333/GM/NIGMS NIH HHS; R01 GM084333-03/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Carboxylic Acids; 0/Halogens; 0/Hexanes; 0/Ions; 0/Ligands; 0/Succinimides; 516-12-1/N-iodosuccinimide
Comments/Corrections

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