Efficient and Highly Enantioselective Aerobic Oxidation-Michael-Carbocyclization Cascade Transformations by Integrated Pd(0)-CPG Nanoparticle/Chiral Amine Relay Catalysis
2014 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 46, no 10, 1303-1310 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2014. Vol. 46, no 10, 1303-1310 p.
asymmetric cocatalysis, aerobic oxidations, relay catalysis, integrated heterogeneous catalysis, integrated homogeneous catalysis, quaternary stereocenters
IdentifiersURN: urn:nbn:se:su:diva-105909DOI: 10.1055/s-0033-1340883ISI: 000336839600003OAI: oai:DiVA.org:su-105909DiVA: diva2:733277
FunderSwedish Research Council