| Stereocontrolled synthesis of α-amino-α'-alkoxy ketones by a copper-catalyzed cross-coupling of peptidic thiol esters and α-alkoxyalkylstannanes. | |
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MedLine Citation:
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PMID: 21675755 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A stereocontrolled synthesis of α-amino-α'-alkoxy ketones is described. This pH-neutral copper(I) thiophene-2-carboxylate (CuTC)-catalyzed cross-coupling of amino acid thiol esters and chiral nonracemic α-alkoxyalkylstannanes gives α-amino-α'-alkoxy ketones in good to excellent yields with complete retention of configuration at the α-amino- and α-alkoxy-substituted stereocenters. |
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Authors:
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Hao Li; Anyu He; John R Falck; Lanny S Liebeskind |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2011-06-15 |
Journal Detail:
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Title: Organic letters Volume: 13 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2011 Jul |
Date Detail:
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Created Date: 2011-07-08 Completed Date: 2011-10-17 Revised Date: 2013-03-21 |
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: 3682-5 Citation Subset: IM |
Copyright Information:
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© 2011 American Chemical Society |
Affiliation:
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Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids Catalysis Copper / chemistry* Esters Hydrogen-Ion Concentration Ketones / chemical synthesis*, chemistry Molecular Structure Organotin Compounds / chemistry* Peptides / chemistry* Stereoisomerism Sulfhydryl Compounds / chemistry Thiophenes / chemistry |
| Grant Support | |
ID/Acronym/Agency:
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GM031278/GM/NIGMS NIH HHS; GM066153/GM/NIGMS NIH HHS; R01 GM066153/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Esters; 0/Ketones; 0/Organotin Compounds; 0/Peptides; 0/Sulfhydryl Compounds; 0/Thiophenes; 527-72-0/thiophene-2-carboxylate; 7440-50-8/Copper |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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