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  • 1
    Electronic Resource
    Electronic Resource
    Chiral Atropisomeric Metalloporphyrins in the Enantioselective Styrene Epoxidation (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1165-1171 
    Details
    ISSN: 1434-193X
    Keywords: Porphyrinoids ; Asymmetric catalysis ; Atropisomerism ; Epoxidation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A new series of porphyrins has been synthesised, incorporating four identical chiral binaphthyl derivatives in the meso-positions. Owing to a hindered rotation around the bond between the naphthyl and the porphyrin, four atropisomers are generated, which were fully separated by preparative TLC and thoroughly characterised. The free bases were metallated with iron(III) and manganese(III) and the resulting complexes were used as catalytic precursors in styrene epoxidation. The reactions show chemoselectivity and enantioselectivity, depending on the stereochemistry of the metalloporphyrin. It is demonstrated that highest efficiency is performed by the ααββ isomer, showing C2 symmetry.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Syntheses, Structures, and Reactivity of 2,5-Diboryl-1-alkylpyrroles and Di(1-alkyl-2-pyrrolyl)boranes (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 399-404 
    Details
    ISSN: 1434-1948
    Keywords: Boranes ; 1-Alkylpyrroles ; Porphyrinogenes ; Lithiation ; Tin-boron exchange ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of 2,5-dilithiated 1-methylpyrrole (1a) with ClB(NR2)2 lead to the novel 2,5-diboryl-1-methylpyrroles 2a and 2b. Accordingly, 2,5-diboryl-1-benzylpyrrole 2d is obtained. 1a and Cl2BNiPr2 form the aminochloroboryl-substituted derivative 2c and the di(5-boryl-2-pyrrolyl)borane 4 in 29% and 15% yield, respectively. The 2,5-distannyl-1-methylpyrrole 1c is used for the synthesis of the aryloxy-boryl derivative 2e. Reacting monolithiated 1-methyl- and 1-benzylpyrroles with Cl2BNiPr2 yields the di(2-pyrrolyl)boranes 3e and 3f, respectively. NMR and MS data are in agreement with the compositions of the compounds, which are confirmed by X-ray structure analyses for 2a, 2b, 2d, und 3e.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
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