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Efficient and Highly Enantioselective Aerobic Oxidation-Michael-Carbocyclization Cascade Transformations by Integrated Pd(0)-CPG Nanoparticle/Chiral Amine Relay Catalysis
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
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2014 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 46, no 10, 1303-1310 p.Article in journal (Refereed) Published
Abstract [en]

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.
Keyword [en]
asymmetric cocatalysis, aerobic oxidations, relay catalysis, integrated heterogeneous catalysis, integrated homogeneous catalysis, quaternary stereocenters
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-105909DOI: 10.1055/s-0033-1340883ISI: 000336839600003OAI: oai:DiVA.org:su-105909DiVA: diva2:733277
Funder
Swedish Research Council
Note

AuthorCount:6;

Available from: 2014-07-08 Created: 2014-07-08 Last updated: 2017-12-05Bibliographically approved

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