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  • Chiral tin hydrides  (2)
  • Cyclizations, intramolecular  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Free-radical Cyclization of Petroselinic Acid (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 203-205 
    Details
    ISSN: 0170-2041
    Keywords: Radicals ; Cyclizations, intramolecular ; Petroselinic acid ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Petroselinic acid was cyclized via methyl 2-iodopetroselinate (1) with tributyltin hydride to give methyl trans- and cis-2-dodecyl-1-cyclopentanecarboxylate (2). The atom-transfer method with hexabutylditin resulted in the formation of bicyclic γ-lactones 4 and methyl trans-2-(1′-iodododecyl)-1-cyclopentanecarboxylate (trans-5). The same products were obtained with the new initiator system SnCl2/AgOAc. This method showed, if compared with the other methods, the shortest reaction time, the highest yield and stereoselectivity combined with a very simple workup procedure and the use of less toxic chemicals.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930136
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  • 2
    Electronic Resource
    Electronic Resource
    Enantioselectivity of the Transfer of Hydrogen Atoms to Acyclic Prochiral Carbon-Centred Radicals Using Chiral Tin Hydrides (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 177-181 
    Details
    ISSN: 1434-193X
    Keywords: Radicals ; Chiral tin hydrides ; Enantioselective radical reactions ; Reductions ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Racemic α-bromo esters 2 have been reduced via prochiral radicals 5 with low to moderate enantioselectivities using chiral tin hydrides 1 with a stereogenic tin atom containing chiral 2-[(1-dimethylaminoalkyl)phenyl] ligands. The tin hydrides 1 were mixtures of diastereomers. It could be shown that the minor diastereomer of tin hydrides 1a and 1b reacts with good enantioselectivity whereas the major diastereomer reacts almost unselectively. The observed enantioselectivities are also strongly influenced by steric effects of the substituents attached to the radical centre.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of Novel Optically Active Tin Hydrides Containing Chiral Ligands (1997)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 1539-1546 
    Details
    ISSN: 0009-2940
    Keywords: Chiral tin hydrides ; Chiral hydrogen donors ; Tin ; Ligand effects ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the chiral tin bromides 1-4 and hydrides 5-8, containing the potentially bidentate, optically active 2-[ (1 S/R)- 1 -dimethylaminoethyl]phenyl and 2 -[( 1 S) - 1 -dimethylamino-2,2-dimethylpropyl]phenyl ligands, is reported. The tin hydrides 5-8, with the tin atom as the stereogenic centre, were isolated as diastereomeric mixtures with diastereomeric ratios of dr = 50:50 up to dr = 80:20. The absolute configuration of ( - ) - (1 S)- 1 - (2-bromophenyl) -2,2-dimethylpropylamine [(S)-10] was determined by single-crystal X-ray structure analysis.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19971301030
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