| Cyanocuprates Convert Carboxylic Acids Directly into Ketones. | |
| | |
MedLine Citation:
|
PMID: 21894954 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
|
Carboxylic acids were converted directly in 56-99% yields into methyl, n-butyl, and isopropyl ketones using excess cyanocuprates R(2)CuLi·LiCN. A substrate with a stereocenter α to the carboxylic acid was converted into ketones with very little loss of enantiomeric purity. A variety of functional groups were tolerated including aryl bromides. This direct transformation of a carboxylic acid into ketone with minimal tertiary alcohol formation is proposed to involve a relatively stable copper ketal tetrahedral intermediate. |
| | |
Authors:
|
Douglas T Genna; Gary H Posner |
Related Documents
:
|
14572664 - Osgstu3 and osgtu4, encoding tau class glutathione s-transferases, are heavy metal- and... 18924904 - Computer-assisted automated synthesis. iii. synthesis of substituted n-(carboxyalkyl) a... 19016884 - Acid trehalase is involved in intracellular trehalose mobilization during postdiauxic g... 16842874 - The acetic acid tolerance response induces cross-protection to salt stress in salmonell... 1151634 - Anticonvulsant activity of n,n'-bis[3-(3-substituted urea)propyl]piperazines. 9135574 - A micromethod for quantitative determination of iodoamino acids in thyroglobulin. |
Publication Detail:
|
Type: JOURNAL ARTICLE Date: 2011-9-6 |
Journal Detail:
|
Title: Organic letters Volume: - ISSN: 1523-7052 ISO Abbreviation: - Publication Date: 2011 Sep |
Date Detail:
|
Created Date: 2011-9-7 Completed Date: - Revised Date: - |
Medline Journal Info:
|
Nlm Unique ID: 100890393 Medline TA: Org Lett Country: - |
Other Details:
|
Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
|
Department of Chemistry, School of Arts and Sciences, The Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218-2685, United States. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
|
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Rhodium-Catalyzed Cross-Coupling Reaction of Arylboronates and Diazoesters and Tandem Alkylation Rea...
Next Document: Intraparticle Charge Delocalization of Carbene-Functionalized Ruthenium Nanoparticles Manipulated by...