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Catalytic Enantioselective beta-Alkylation of alpha,beta-Unsaturated Aldehydes by Combination of Transition-Metal- and Aminocatalysis: Total Synthesis of Bisabolane Sesquiterpenes
Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap, teknik och matematik.ORCID-id: 0000-0002-5108-6487
Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap, teknik och matematik.
Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap, teknik och matematik.
Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden.
Vise andre og tillknytning
2011 (engelsk)Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, nr 32, s. 8784-8788Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Branching out! The first co-catalytic enantioselective (up to 98:2 e.r.) β-alkylation of α,β-unsaturated aldehydes by combination of simple chiral amine and copper catalysts provides β-branched aldehydes in a one-pot protocol (see scheme). The methodology was applied to the short total syntheses of bisabolane sesquiterpenes (S)-(+)-curcumene, (E)-(S)-(+)-3- dehydrocurcumene and (S)-(+)-tumerone. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

sted, utgiver, år, opplag, sider
2011. Vol. 17, nr 32, s. 8784-8788
Emneord [en]
aldehydes; alkylation; asymmetric conjugate additions; enantioselectivity; co-catalysis; zinc
HSV kategori
Identifikatorer
URN: urn:nbn:se:miun:diva-14528DOI: 10.1002/chem.201100756ISI: 000294704700003Scopus ID: 2-s2.0-79960754105OAI: oai:DiVA.org:miun-14528DiVA, id: diva2:443350
Tilgjengelig fra: 2011-09-23 Laget: 2011-09-23 Sist oppdatert: 2017-12-08bibliografisk kontrollert
Inngår i avhandling
1. Development of highly enantioselective organocatalyzed transformations
Åpne denne publikasjonen i ny fane eller vindu >>Development of highly enantioselective organocatalyzed transformations
2011 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
sted, utgiver, år, opplag, sider
Sundsvall: Mid Sweden University, 2011. s. 48
Serie
Mid Sweden University doctoral thesis, ISSN 1652-893X ; 117
Emneord
Asymetric catalysis, aldehydes, proline derivatives, transition metals, Friedel-Crafts, conjugate addition, boration, α-alkylation
HSV kategori
Identifikatorer
urn:nbn:se:miun:diva-15621 (URN)978-91-86694-61-6 (ISBN)
Veileder
Tilgjengelig fra: 2011-12-22 Laget: 2011-12-22 Sist oppdatert: 2012-07-30bibliografisk kontrollert
2. Development of catalytic enantioselective C-C bond-forming and cascade transformations by merging homogeneous or heterogeneous transition metal catalysis with asymmetric aminocatalysis
Åpne denne publikasjonen i ny fane eller vindu >>Development of catalytic enantioselective C-C bond-forming and cascade transformations by merging homogeneous or heterogeneous transition metal catalysis with asymmetric aminocatalysis
2014 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Sundsvall: Mid Sweden University, 2014. s. 70
Serie
Mid Sweden University doctoral thesis, ISSN 1652-893X ; 206
Emneord
asymmetric catalysis, transition metals, aldehydes, heterogeneous catalysis, amino acid, organocatalysis, α-allylation, β-alkylation, dynamic transformations, polysubstituted, carbocycles, spirocyclic oxindoles, all-carbon quaternary stereocenters
HSV kategori
Identifikatorer
urn:nbn:se:miun:diva-23605 (URN)978-91-87557-90-3 (ISBN)
Disputas
2014-10-24, 10:15 (engelsk)
Opponent
Veileder
Tilgjengelig fra: 2014-12-05 Laget: 2014-12-05 Sist oppdatert: 2016-09-29bibliografisk kontrollert

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