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Highly Enantioselective Cascade Transformations by Merging Heterogeneous Transition Metal Catalysis with Asymmetric Aminocatalysis
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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2012 (English)In: Scientific Reports, ISSN 2045-2322, E-ISSN 2045-2322, Vol. 2, 851- p.Article in journal (Refereed) Published
Abstract [en]

The concept of combining heterogeneous transition metal and amine catalysis for enantioselective cascade reactions has not yet been realized. This is of great advantage since it would allow for the recycling of expensive and non-environmentally friendly transition metals. We disclose that the use of a heterogeneous Pd-catalyst in combination with a simple chiral amine co-catalyst allows for highly enantioselective cascade transformations. The preparative power of this process has been demonstrated in the context of asymmetric cascade Michael/carbocyclization transformations that delivers cyclopentenes bearing an all carbon quaternary stereocenters in high yields with up to 30: 1 dr and 99% ee. Moreover, a variety of highly enantioselective cascade hetero-Michael/carbocyclizations were developed for the one-pot synthesis of valuable dihydrofurans and pyrrolidines (up to 98% ee) by using bench-stable heterogeneous Pd and chiral amines as co-catalysts.

Place, publisher, year, edition, pages
2012. Vol. 2, 851- p.
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-83802DOI: 10.1038/srep00851ISI: 000311100900004OAI: oai:DiVA.org:su-83802DiVA: diva2:577169
Funder
Swedish Research Council
Note

AuthorCount:6;

Available from: 2012-12-14 Created: 2012-12-14 Last updated: 2017-12-06Bibliographically approved
In thesis
1. Development of Catalytic Enantioselective Approaches for the Synthesis of Carbocycles and Heterocycles
Open this publication in new window or tab >>Development of Catalytic Enantioselective Approaches for the Synthesis of Carbocycles and Heterocycles
2013 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

In biological systems, most of the active organic molecules are chiral. Some of the main constituents of living organisms are amino acids and sugars. They exist predominantly in only one enantiomerically pure form. For example, our proteins are built-up by L-amino acids and as a consequence they are enatiomerically pure and will interact in different ways with enantiomers of chiral molecules. Indeed, different enantiomers or diastereomers of a molecule could often have a drastically different biological activity. It is of paramount importance in organic synthesis to develop new routes to control and direct the stereochemical outcome of reactions. The aim of this thesis is to investigate new protocols for the synthesis of complex chiral molecules using simple, environmentally friendly proline-based organocatalysts. We have investigated, the aziridination of linear and branched enals, the stereoselective synthesis of β-amino acids with a carbene co-catalyst, the synthesis of pyrazolidines, the combination of heterogeneous transition metal catalysis and amine catalysis to deliver cyclopentenes bearing an all-carbon quaternary stereocenter and a new heterogeneous dual catalyst system for the carbocyclization of enals. The reactions presented in this thesis afforded the corresponding products with high levels of chemo-, diastero- and enantioselectivity.

Place, publisher, year, edition, pages
Stockholm: Department of Organic Chemistry, Stockholm University, 2013. 75 p.
Keyword
Organocatalysis, Asymmetric Catalysis, Heterogeneous Catalysis, Aziridines, Pyrazolidines, Cyclopentanes
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-94680 (URN)978-91-7447-781-8 (ISBN)
Public defence
2013-12-04, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (English)
Opponent
Supervisors
Note

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 5: Submitted. 

Available from: 2013-11-12 Created: 2013-10-08 Last updated: 2014-09-24Bibliographically approved

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