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Efficient and highly enantioselective aerobic oxidation-michael- carbocyclization cascade transformations by integrated Pd(0)-CPG nanoparticle/chiral amine relay catalysis
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden .
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden .
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden .
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5108-6487
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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. © Georg Thieme Verlag Stuttgart.New York.

Place, publisher, year, edition, pages
2014. Vol. 46, no 10, 1303-1310 p.
Keyword [en]
aerobic oxidations, asymmetric cocatalysis, integrated heterogeneous catalysis, integrated homogeneous catalysis, quaternary stereocenters, relay catalysis
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-22040DOI: 10.1055/s-0033-1340883ISI: 000336839600003Scopus ID: 2-s2.0-84900490413OAI: oai:DiVA.org:miun-22040DiVA: diva2:720701
Note

Language of Original Document: English

Available from: 2014-06-02 Created: 2014-05-30 Last updated: 2016-09-29Bibliographically approved

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