title: Catalytic aerobic oxidation and tandem enantioselective cycloaddition in cascade multicomponent synthesis.
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.
authors: Max-Planck-Institut für Molekulare Physiologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany), Fax: (+49) 231-133-2499; Fakultät Chemie und Chemische Biologie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44227 Dortmund (Germany).
authors: Marco
authors: M
authors: Potowski
authors: Christian
authors: C
authors: Merten
authors: Andrey P
authors: AP
authors: Antonchick
authors: Herbert
authors: H
authors: Waldmann
keywords: aerobic oxidation; asymmetric catalysis; azomethine; cycloaddition; ylides alkylation