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A palladium/chiral amine co-catalyzed enantioselective dynamic cascade reaction: Synthesis of polysubstituted carbocycles with a quaternary carbon stereocenter
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5108-6487
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden .
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden .
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2013 (English)In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 23, p. 6050-6054Article in journal (Refereed) Published
Abstract [en]

Polysubstituted 5- and 6-membered carbocycles were synthesized by the title reaction. The one-pot dynamic relay process generates four new stereocenters, including a quaternary carbon center, in a highly enantioselective fashion (99.5:0.5→99:0.5 e.r.) by using a simple combination of palladium and chiral amine co-catalysts. 

Place, publisher, year, edition, pages
2013. Vol. 52, no 23, p. 6050-6054
Keywords [en]
aldehydes, asymmetric catalysis, carbocycles, co-catalysis, quaternary carbon stereocenters
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-19359DOI: 10.1002/anie.201300559ISI: 000319742400028Scopus ID: 2-s2.0-84878387915OAI: oai:DiVA.org:miun-19359DiVA, id: diva2:645717
Note

:doi 10.1002/anie.201300559

Available from: 2013-09-05 Created: 2013-06-19 Last updated: 2017-12-06Bibliographically approved
In thesis
1. Development of catalytic enantioselective C-C bond-forming and cascade transformations by merging homogeneous or heterogeneous transition metal catalysis with asymmetric aminocatalysis
Open this publication in new window or tab >>Development of catalytic enantioselective C-C bond-forming and cascade transformations by merging homogeneous or heterogeneous transition metal catalysis with asymmetric aminocatalysis
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Chiral molecules play a central role in our daily life and in nature, for instance the different enantiomers or diastereomers of a chiral molecule may show completely different biological activity. For this reason, it is a vital goal for synthetic chemists to design selective and efficient methodologies that allow the synthesis of the desired enantiomer. In this context, it is highly important that the concept of green chemistry is considered while designing new approaches that eventually will provide more environmental and sustainable chemical synthesis.The aim of this thesis is to develop the concept of combining transition metal catalysis and aminocatalysis in one process (dual catalysis). This strategy would give access to powerful tools to promote reactions that were not successful with either transition metal catalyst or the organocatalyst alone. The protocols presented in this thesis based on organocatalytic transformations via enamine or iminium intermediates or both, in combination with transition metal catalysis, describes new enantioselective organocatalytic procedures that afford valuable compounds with high chemo- and enantioselectivity from inexpensive commercial available starting materials. In paper I, we present a successful example of dual catalysis: the combination of transition metal activation of an electrophile and aminocatalyst activation of a nucleophile via enamine intermediate. In paper II, the opposite scenario is presented, here the transition metal activates the nucleophile and the aminocatalyst activates the electrophile via an iminium intermediate. In paper III,we present a domino Michael/carbocyclisation reaction that is catalysed by a chiral amine (via iminium/enamine activation) in combination with a transition metal catalysts activation of an electrophile. In paper IV, the concept of dual catalysis was further extended and applied for the highly enantioselective synthesis of valuable structural scaffolds, namely poly-substituted spirocyclic oxindoles. Finally, in paper V the concept of dual catalysis was expanded, by investigating more challenging and environmentally benign processes, such as the successful combination of a heterogeneous palladium and amine catalysts for the highly enantioselective synthesis of functionalised cyclopentenes, containing an all carbonquaternary stereocenter, dihydrofurans and dihydropyrrolidines.

Place, publisher, year, edition, pages
Sundsvall: Mid Sweden University, 2014. p. 70
Series
Mid Sweden University doctoral thesis, ISSN 1652-893X ; 206
Keywords
asymmetric catalysis, transition metals, aldehydes, heterogeneous catalysis, amino acid, organocatalysis, α-allylation, β-alkylation, dynamic transformations, polysubstituted, carbocycles, spirocyclic oxindoles, all-carbon quaternary stereocenters
National Category
Natural Sciences Chemical Sciences
Identifiers
urn:nbn:se:miun:diva-23605 (URN)978-91-87557-90-3 (ISBN)
Public defence
2014-10-24, 10:15 (English)
Opponent
Supervisors
Available from: 2014-12-05 Created: 2014-12-05 Last updated: 2016-09-29Bibliographically approved

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Ma, GuangningAfewerki, SamsonIbrahem, IsmailCórdova, Armando

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