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  • 1
    ISSN: 1434-193X
    Keywords: Amino ketones ; Homogeneous catalysis ; Aziridination ; Copper ; Enols ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---A series of acyclic and cyclic enol derivatives 1 has been transformed into the corresponding α-amino-functionalized ketones 2 by means of enantioselective catalytic aziridination with chiral Cu complexes, prepared in situ from [Cu(MeCN)4]PF6 and the optically active ligands 3, by using (N-tosylimino)iodobenzene (PhINTs) as a nitrogen source. The best enantioselectivities (ee values of up to 52%) have been achieved for the electronically deactivated enol acetate 1aδ, but the incorporation of steric bulk and the substitution pattern at the enol double bond do not improve the ee values. The cyclic substrates react considerably less readily (only up to 45% conversion) compared to their acyclic counterparts (complete consumption). A transition structure is suggested for the asymmetric Cu-catalyzed aziridination of the enol acetate 1aδ in the presence of the chiral ligand 3b that could account for the sense of the (R)-configured product 2a.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Publication Date: 2003-05-10
    Description: 〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Bardelli, Alberto -- Parsons, D Williams -- Silliman, Natalie -- Ptak, Janine -- Szabo, Steve -- Saha, Saurabh -- Markowitz, Sanford -- Willson, James K V -- Parmigiani, Giovanni -- Kinzler, Kenneth W -- Vogelstein, Bert -- Velculescu, Victor E -- CA43460/CA/NCI NIH HHS/ -- CA57345/CA/NCI NIH HHS/ -- CA62924/CA/NCI NIH HHS/ -- New York, N.Y. -- Science. 2003 May 9;300(5621):949.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉The Howard Hughes Medical Institute and The Sidney Kimmel Comprehensive Cancer Center at Johns Hopkins, Baltimore, MD 21231, USA.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/12738854" target="_blank"〉PubMed〈/a〉
    Keywords: Amino Acid Sequence ; Colorectal Neoplasms/*enzymology/*genetics ; Computational Biology ; *DNA Mutational Analysis ; Exons ; Fusion Proteins, gag-onc/genetics ; Guanylate Cyclase/genetics ; Humans ; Molecular Sequence Data ; Mutation ; Polymerase Chain Reaction ; Protein Structure, Tertiary ; Protein-Tyrosine Kinases/chemistry/*genetics/metabolism ; Receptor, EphA3/genetics ; Receptor, trkB/genetics ; Receptor, trkC/genetics ; Sequence Analysis, DNA ; Vascular Endothelial Growth Factor Receptor-2/genetics
    Print ISSN: 0036-8075
    Electronic ISSN: 1095-9203
    Topics: Biology , Chemistry and Pharmacology , Computer Science , Medicine , Natural Sciences in General , Physics
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