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  • 1
    Electronic Resource
    Electronic Resource
    Diastereo- and Regioselective Intramolecular Heck Reaction of α-Amino Alcohol Derivatives for the Synthesis of Enantiomerically Pure Isoquinolines and Benzazepines at Ambient and High Pressure (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1407-1413 
    Details
    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
    URL: http://dx.doi.org/10.1002/jlac.199719970718
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  • 2
    Electronic Resource
    Electronic Resource
    Intramolecular Heck Reaction for the Synthesis of Isochromanes under Ambient and High pressure (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 887-891 
    Details
    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
    URL: http://dx.doi.org/10.1002/jlac.199719970516
    Library Location Call Number Volume/Issue/Year Availability
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    Paper (German National Licenses)
    Fulltext
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