Journal
SYNTHESIS-STUTTGART
Volume 46, Issue 10, Pages 1303-1310Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1340883
Keywords
asymmetric cocatalysis; aerobic oxidations; relay catalysis; integrated heterogeneous catalysis; integrated homogeneous catalysis; quaternary stereocenters
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Funding
- European Union
- Mid Sweden University
- Swedish National Research Council
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A series of highly diastereo- and enantioselective aerobic oxidation-Michael-carbocyclization cascade transformations by integrated heterogeneous Pd(0)-CPG nanoparticle/chiral amine relay catalysis are disclosed. The heterogeneous Pd(0)-CPG nanoparticle catalysts were efficient for both the sequential aerobic oxidation and dynamic kinetic asymmetric Michael-carbocyclization transformations, resulting in 1) oxidation of a variety of allylic alcohols to enals and 2) formation of cyclopentenes containing an all-carbon quaternary stereocenter in good to high yields with up to 20:1 dr and 99.5:0.5 er.
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