Document Detail


Stereocontrolled synthesis of α-amino-α'-alkoxy ketones by a copper-catalyzed cross-coupling of peptidic thiol esters and α-alkoxyalkylstannanes.
MedLine Citation:
PMID:  21675755     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Hao Li; Anyu He; John R Falck; Lanny S Liebeskind
Related Documents :
23651115 - Map (2.0) 3d: a sequence/structure based server for protein engineering.
22147685 - Guest-responsive covalent frameworks by the cross-linking of liquid-crystalline salts: ...
18960645 - Microdetermination of nitrates and nitramines-i titrimetric methods based on the reduct...
18960365 - Adsorption of cations from formic acid solutions on strong acid cation-exchange resin. ...
21592665 - The repellent effect of organic fatty acids on culicoides midges as determined with suc...
21685295 - Genetic and biochemical analysis of padr-padc promoter interactions during the phenolic...
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2011-06-15
Journal Detail:
Title:  Organic letters     Volume:  13     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2011 Jul 
Date Detail:
Created Date:  2011-07-08     Completed Date:  2011-10-17     Revised Date:  2013-06-28    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3682-5     Citation Subset:  IM    
Copyright Information:
© 2011 American Chemical Society
Affiliation:
Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
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:
GM031278/GM/NIGMS NIH HHS; GM066153/GM/NIGMS NIH HHS; R01 GM066153/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
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


Previous Document:  Concise Total Synthesis of (-)-8-Epigrosheimin.
Next Document:  Adsorption of Pb(II) on O2 Plasma Oxidized Multi-Walled Carbon Nanotubes: Thermodynamics, Kinetics, ...