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Catalytic Aerobic Oxidation and Tandem Enantioselective Cycloaddition in Cascade Multicomponent Synthesis
Author(s) -
Potowski Marco,
Merten Christian,
Antonchick Andrey P.,
Waldmann Herbert
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500125
Subject(s) - enantioselective synthesis , cycloaddition , stereocenter , catalysis , cascade reaction , cascade , chemistry , tandem , combinatorial chemistry , cyclopentadiene , organic chemistry , materials science , chromatography , composite material
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 CH 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.