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  • Organic Chemistry  (2)
  • 104-643A; DEPTH, sediment/rock; DRILL; Drilling/drill rig; DSDP/ODP/IODP sample designation; Grain size, sieving; Joides Resolution; Leg104; Norwegian Sea; Ocean Drilling Program; ODP; Sample code/label; Size fraction 〉 0.063 mm, sand; Size fraction 〉 1 mm, gravel; Size fraction 0.125-0.063 mm, 3.0-4.0 phi, very fine sand; Size fraction 0.500-0.125 mm, 1.0-3.0 phi; Size fraction 1.000-0.500 mm, 0.0-1.0 phi, coarse sand
  • 1995-1999  (2)
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  • 1
    ISSN: 0947-3440
    Keywords: Heck reaction, intramolecular ; α-Amino acids ; Isoquinolines ; Palladium ; Heterocycles ; Synthesis, enantioselective ; High pressure ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Alkylation and acylation of the alkenes 9b, c and 10a, b, which are easily prepared from the corresponding α-amino alcohols, with 2-halobenzyl and 2-halobenzoyl halides respectively, gives 11-15. These compounds cyclize with excellent diastereo- and regioselectivity to the enantiomerically pure N-heterocycles 18-20 in an intramolecular Heck reaction using 5 mol-% of Pd(OAc)2 in the presence of PPh3, TPAB and KOAc. Under the same conditions substrate 17 leads to the enantiomerically pure benzazepine 24. The reaction of the bromoarene derivatives 14-15 must be performed under high pressure to give good results.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 887-891 
    ISSN: 0947-3440
    Keywords: Heck reaction, intramolecular ; Isochromane ; Palladium ; Heterocycles ; High-pressure chemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The iodoarenes 9 and 10, bearing (E)- and (Z)-alkene moieties, respectively, easily prepared by alkylation of the corresponding alcohols 7a-c and 8a-c with 2 iodobenzyl iodide, undergo intramolecular Heck reactions to give the isochromanes 12-15a-c in good yields. The selectivity of the reaction depends on the size of the substituent R in 9 and 10; increasing bulkiness of R leads to a decrease in diastereoselectivity and an increase in regioselectivity. High-pressure experiments confirm the proposed mechanism and show that bromoarenes such as 11, which tend to be unreactive at ambient pressure, give good results when the cyclisation is performed under high pressure.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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