Catalytic Aerobic Oxidation and Tandem Enantioselective Cycloaddition in Cascade Multicomponent Synthesis |
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Authors: | Marco Potowski Dr Christian Merten Dr Andrey P Antonchick Prof?Dr Herbert Waldmann |
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Institution: | 1. Max‐Planck‐Institut für Molekulare Physiologie, Otto‐Hahn‐Strasse 11, 44227 Dortmund (Germany), Fax: (+49) 231‐133‐2499;2. Fakult?t Chemie und Chemische Biologie, Technische Universit?t Dortmund, Otto‐Hahn‐Strasse 6, 44227 Dortmund (Germany);3. Fakult?t für Chemie und Biochemie, Ruhr‐Universit?t Bochum, Universit?tsstrasse 150, 44799 Bochum (Germany) |
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Abstract: | An efficient multicomponent cascade transformation for the highly diastereo‐ and enantioselective synthesis of complex natural product inspired polycyclic products from simple starting materials is described. The cascade is initiated by copper‐catalyzed aerobic C?H oxidation of cyclopentadiene to cyclopentadienone followed by double catalytic asymmetric 1,3‐dipolar cycloaddition of azomethine ylides. The cascade synthesis efficiently yields structurally complex 5,5,5‐tricyclic products with eight stereocenters with good yields and excellent diastereo‐ and enantiocontrol using one catalyst. |
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Keywords: | aerobic oxidation asymmetric catalysis azomethine cycloaddition ylides alkylation |
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