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  • 1
    ISSN: 1434-193X
    Keywords: 1β-Methylcarbapenems ; Palladium ; Ruthenium ; Catalysis ; Cyclizations ; Stereoselective hydrogenation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -An efficient diastereoselective multi-step synthesis of bicyclic 1β-methylcarbapenem antibiotic precursors has been developed, starting from the commercially available 4-acetoxyazetidin-2-one 4. Chiral ruthenium catalysts are used in the hydrogenation step to control the β-stereochemistry at the 1-position, and a π-allylpalladium ring-closure strategy is used to form the functionalized carbapenem skeleton.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1434-193X
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -No Abstract.
    Type of Medium: Electronic Resource
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  • 3
    ISSN: 1434-193X
    Keywords: Asymmetric synthesis ; Grignard reactions ; Dynamic kinetic resolution ; Asymmetric synthesis ; Unsymmetrical 1,2-diamines ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---A diastereoselective synthesis of tert-butyl-1,2-diamines has been developed from the addition of tert-butylmagnesium chloride to the 1,2-bisimines derived from glyoxal and chiral amines such as 1-(S)-ethylphenylamine, 1-(S)-phenylpropylamine or 1-(S)-(p-chlorophenyl)ethylamine. The influence of solvent, temperature and chiral auxiliaries on the chemical reactivity and stereoselectivity has been fully studied. Evidence of a dynamic kinetic resolution during the bis-addition process of the organometallic, leading to the 1,2-di-tert-butylethanediamine,[1] as a single diastereomer, has been demonstrated. This resolution has been applied with high diastereoselectivities to the synthesis of unsymmetrical disubstituted 1,2-diamines, by addition of one equivalent of tert-butylmagnesium chloride, followed by one equivalent of a second Grignard reagent. Several chiral 1-tert-butyl-1,2-diamines have also been synthesized by monoaddition of tert-butylmagnesium chloride to the bisimines, followed by hydride reduction of the chiral intermediate imines.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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