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  • 1
    Digitale Medien
    Digitale Medien
    α-Metalated Isocyanides in Organic Synthesis. New synthetic methods (6) (1974)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 13 (1974), S. 789-804 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Isocyanides ; Synthetic methods ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: α-Alkali-metalated isocyanides, which can be obtained from isocyanides and bases, can be used for nucleophilic introduction of (masked) α-aminoalkyl groups. Intramolecular ring-closure may then follow if a nucleophile combines at the electron sextet of the isocyanide carbon. Treatment of α-alkali-metalated isocyanides with electrophilic agents permits rapid and efficient synthesis of, inter alia, 2- and 3-amino alcohols, straight-chain, branched, and β-functional α-amino acids, olefins, vinyl isocyanides, and of a large number of mainly five-, but also six- and seven-membered aza-, diaza-, oxa-aza-, and thia-aza heterocycles.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.197407891
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  • 2
    Digitale Medien
    Digitale Medien
    The Homoaldol Reaction, or How to Overcome Problems of Regio- and Stereo-selectivityMetalated Nitrogen Derivatives of Carbonic Acid in Organic Synthesis, Part 28. - Part 27: [72b].Dedicated to Professor Wolfgang Lüttke on the occasion of his 65th birthday (1984)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 23 (1984), S. 932-948 
    Details
    ISSN: 0570-0833
    Schlagwort(e): Homoaldol reaction ; Stereoselectivity ; Synthetic methods ; Regioselectivity ; Chemistry ; General Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Even today, there are conspicuous gaps in the register of organic synthetic methods. Thus, numerous types of homoenolate reagents are listed; yet no generally applicable method for the homologue of the aldol addition, viz. the homoaldol addition, is to be found. The methods documented up to 1980 offer only singular solutions, and, moreover, are not stereoselective. The present article gives an overview of the existing possibilities and then describes how the gap can be closed by using a new class of homoenolate reagents: 2-alkenyl esters of N,N-diisopropylcarbamic acid are lithiated and the resulting allyllithium compounds tailored to high regio- and diastereoselectivity in addition reactions to the carbonyl group via metal exchange. Altogether, the homoaldol reactions now offer a general and reliable, highly stereoselective entry to γ-hydroxycarbonyl compounds, whereby the C(β)—C(γ) bond is formed. Furthermore, it is demonstrated how problems associated with the application of allyl anions as synthetic reagents can be solved today.
    Zusätzliches Material: 2 Ill.
    Materialart: Digitale Medien
    URL: http://dx.doi.org/10.1002/anie.198409321
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