| Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes. | |
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MedLine Citation:
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PMID: 17217307 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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N-heterocyclic carbenes catalyze the oxidation of allylic, propargylic, and benzylic alcohols to esters with manganese(IV) oxide in excellent yields. A variety of ester derivatives can be synthesized, including protected carboxylates. This one-pot tandem oxidation represents the first organocatalytic oxidation of alcohols to esters. Saturated esters can also be accessed from aldehydes using this method. Through the utilization of a chiral catalyst, the acyl-heteroazolium intermediate becomes a chiral acylating agent, which can desymmetrize meso-1,2-diols. [reaction: see text]. |
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Authors:
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Brooks E Maki; Audrey Chan; Eric M Phillips; Karl A Scheidt |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Organic letters Volume: 9 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2007 Jan |
Date Detail:
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Created Date: 2007-01-12 Completed Date: 2007-03-19 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 371-4 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Allyl Compounds
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chemistry* Benzyl Alcohols / chemistry* Catalysis Esters / chemical synthesis*, chemistry Heterocyclic Compounds / chemistry* Hydrocarbons / chemistry Methane / analogs & derivatives*, chemistry Molecular Structure Oxidation-Reduction Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Allyl Compounds; 0/Benzyl Alcohols; 0/Esters; 0/Heterocyclic Compounds; 0/Hydrocarbons; 2465-56-7/carbene; 74-82-8/Methane |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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