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  • Chiral hydrogen donors  (1)
  • Cyclizations, intramolecular  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 203-205 
    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
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 130 (1997), S. 1539-1546 
    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
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