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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of γ-Amino- and δ-Amino-Functionalised Ethers, Amines, or Silanes by Hydroaminomethylation of Heterofunctionalised Allylic Compounds (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 653-660 
    Details
    ISSN: 1434-193X
    Keywords: Hydroaminomethylation ; Rhodium ; Catalysis ; Carbonylation ; Heterofunctionalised allylic compounds ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Heterofunctionalised allylic ethers 1, silanes 5, and amines 9 are hydroformylated in the presence of primary or secondary amines 2 to form the corresponding γ-amino- and δ-amino-functionalised compounds. The rhodium(I)-catalysed reaction sequence proceeds by aldehyde formation and subsequent reductive amination to generate the corresponding functionalised secondary or tertiary amines. This selective one-pot hydroaminomethylation procedure establishes access to γ-amino- and δ-amino-functionalised ethers, amines or silanes with potential biological activity.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Tandem Silylformylation/Wittig Olefination of Terminal Alkynes: Stereoselective Synthesis of 2,4-Dienoic Esters (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1131-1135 
    Details
    ISSN: 1434-193X
    Keywords: Carbonylation ; Wittig reactions ; Rhodium ; Homogeneous catalysis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The rhodium(I)-catalysed sequential silylformylation/Wittig olefination of terminal alkynes with hydrosilanes and carbon monoxide in the presence of stabilised P-ylides leads to substituted 2,4-dienoic esters in a one-pot procedure. The α,β,γ,δ-unsaturated esters are generated with high (2E,4Z) stereoselectivity in good to excellent yields. Conversions of the products in [2+1] cycloaddition reactions are presented.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Stereospezifische Umwandlungen des (+)-2- und (+)-3-Carens in optisch aktive Siebenring-Systeme (1991)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 124 (1991), S. 191-198 
    Details
    ISSN: 0009-2940
    Keywords: Iron complexes ; Carbonylation ; Carene ; Cycloheptanes ; Bicyclo[4.1.1]octanes ; Bicyclo[3.2.1]octanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Stereospecific Conversions of (+)-2- and (+)-3-Carene into Optically Active Seven-Membered Ring SystemsThe reactions of (+)-2-carene (6b) and (+)-3-carene (15) with iron carbonyls are studied under various conditions. Besides double bond isomerization and interconversion of the two isomeric hydrocarbons, at least two different modes of ring opening leading to six- and seven-membered ring products are observed. Under mild conditions the primary ring opening complex 7b is isolated without loss of sterical information. Carbonylation of 7b under various conditions yields optically active cycloheptane systems 18, 19, and 20 or the bicyclic systems 9b and 10b.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19911240128
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  • 4
    Electronic Resource
    Electronic Resource
    Carbonylierende Ringerweiterung, 4. Diastereoselektive Synthesen von Bicyclo[3.2.1]oct-3-en-2,8-dionen durch doppelte Carbonylierung von (R)-(-)-α-Phellandren (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 1079-1087 
    Details
    ISSN: 0009-2940
    Keywords: Ring enlargement ; Phellandrene ; Carbonylation ; Bicyclo[3.2.1]octanes, stereoselective syntheses of ; Iron complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Carbonylating Ring Enlargement, 41). - Diastereoselective Syntheses of Bicyclo[3.2.l]oct-3-ene-2,8-diones by Double Carbonylation of (It)-(-)-α-PhellandreneIn order to clarify the stereochemistry of the carbonylating ring enlargement of cyclohexadiene complexes 1 to complexed seven-membered ring ketones 2 and the further carbonylation to bicyclo[3.2.1]oct-3-ene-2,8-diones 3 the exo and endo isomers of (R)-(-)-α-phellandrene complex 7 were synthesized in pure form and in various isomeric ratios and converted. The optically active ring-enlargement products 11 and 12 obtained therefrom, as well as the enantiomerically pure bicyclooctenes 20-22, implicate a stereospecific reaction course under retention of the configuration predetermined by the starting material 6 and its complexes 7. This was confirmed by an X-ray determination of the absolute configuration of exo-12. Thus, the method is suitable for the diastereoselective synthesis of bicyclo[3.2.1]oct-3-ene-2,8-diones 3 from 1,3-cyclohexadiene complexes 1.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230522
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  • 5
    Electronic Resource
    Electronic Resource
    Carbonylierende Ringerweiterung, 5. Enantioselektive Synthese des Bicyclo[3.2.1]oct-3-en-2,8-dion-Systems durch doppelte Carbonylierung von α-Terpinen und anderen prochiralen Cyclohexadienen (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 1089-1095 
    Details
    ISSN: 0009-2940
    Keywords: Ring enlargement ; Carbonylation ; Enantioselective synthesis ; Iron complexes ; Bicyclo[3.2.1]octanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Carbonylating Ring Enlargement, 51). - Enantioselective Synthesis of the Bicyclo[3.2.l]oct-3-ene-2,8-dione Systems by Double Carbonylation of α-Terpinene and Other Prochiral CyclohexadienesThe steric information in tricarbonyl iron complexes of type 2(R1 ≠ R2), established during the complexation of prochiral 1,3-cyclohexadienes can be transferred to bicyclo[3.2.1]oct-3-ene-2,8-diones by metal-induced ring enlargement and bridging carbonylation. This was verified by the synthesis and conversion of optically active tricarbonyl iron complexes 2 of α-terpinene (1). These complexes can be either obtained by chirality transfer during complexation and rearrangement of (R)-(+)- or (S)-(-)-limonene (7) or by separation of racemic mixtures on triacetyl cellulose. The separation on chiral phases and subsequent stereoselective conversion to bicyclo[3.2.1]oct-3-ene-2,8-diones may also be carried out with other tricarbonyl iron complexes of prochiral cyclohexadienes (lacking additional functional groups).
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230523
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  • 6
    Electronic Resource
    Electronic Resource
    Carbonylierende Ringerweiterung, 3. Stereochemie der Komplexierung und carbonylierenden Ringerweiterung von 1,3,5-Trimethyl-1,3-cyclohexadien (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 1071-1078 
    Details
    ISSN: 0009-2940
    Keywords: Carbonylation ; Ring enlargement ; Cyclohexadiene ; Iron complexes ; Bicyclo[3.2.1]octane skeleton ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Carbonylating Ring Enlargement, 31). - Stereochemistry of Complexation and Carbonylating Ring Enlargement of 1,3,5-Trimethyl-1,3-cyclohexadieneThe stereochemical course of the complexation and the metal- and Lewis acid induced carbonylating ring enlargement of cyclohexadienes 1 to bicyclo[3.2.1]oct-3-ene-2,8-diones 4 via diene iron tricarbonyl complexes 2 and complexed sevenmembered ring ketones 3 is investigated by synthesis and conversion of the diastereomeric complexes exo- and endo-12 of 1,3,5-trimethyl-1,3-cyclohexadiene (7). It can be concluded, that the stereochemical information of the starting materials can be transferred to the product. In the first step exo and endo substituents retain their relative position towards the metal. The introduction of the second carbon monoxide unit and ketone bridge formation also occurs stereospecifically from the side of the complexing metal without loosing the preestablished position of the substituents. Mechanistic aspects of these results are discussed.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230521
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